Amidine compounds and use thereof for plant disease control

ABSTRACT

An amidine compound represented by formula (1): wherein R 1  represent a C1-C11 fluoroalkyl group, a C3-C11 fluoroalkenyl group or a C3-C11 fluoroalkynyl group; R 2  represent a C1-C3 alkyl group; R 3  represent a C1-C3 alkyl group; R 4  represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens and R 5  represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens, said compound having excellent plant disease controlling effect.

TECHNICAL FIELD

The present invention relates to amidine compounds and use thereof for plant disease control.

BACKGROUND ART

Hitherto, agents for controlling plant diseases have been developed, and compounds having a plant disease controlling effect have been found and put to practical use.

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide a compound having excellent plant disease controlling effect.

Means for Solving the Problems

As a result of intensive research conducted by the present inventors in an attempt to find compounds having excellent plant disease controlling effect, it has been found that amidine compounds represented by the following formula (1) have excellent plant disease controlling effect. Thus, the present invention has been accomplished.

That is, the present invention provides:

[1] An amidine compound represented by the formula (1):

wherein R¹ represent a C1-C11 fluoroalkyl group, a C3-C11 fluoroalkenyl group or a C3-C11 fluoroalkynyl group; R² represent a C1-C3 alkyl group; R³ represent a C1-C3 alkyl group; R⁴ represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens and R⁵ represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens (hereinafter referred to as the present compound); [2] The amidine compound according to above [1], wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group having one or more halogens; [3] The amidine compound according to above [1], wherein R⁴ is a C1-C6 alkyl group and R⁵ is a C1-C6 alkyl group; [4] A plant disease controlling agent, which comprises the amidine compound according to above [1] as an active ingredient; [5] A method for controlling plant diseases, which comprises the step of applying an effective amount of the amidine compound according to above [1] to plants or soils; and [6] Use of the amidine compound according to above [1] for controlling plant diseases.

Effect of the Invention

The present compound has excellent plant disease controlling effect, and hence is useful as an active ingredient of plant disease controlling agents.

MODE FOR CARRYING OUT THE INVENTION

The explanation of substituents of the present invention is as follows.

The C1-C11 fluoroalkyl group represents the C1-C11 alkyl group having one or more fluorines.

Examples of the C1-C11 fluoroalkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a heptafluoropropyl group, a 3,3,3-trifluoropropyl group, a 2-fluorobutyl group, a 4-fluorobutyl group, a 2,4-difluorobutyl group, a 2,2,4-trifluorobutyl group, a 2,4,4-trifluorobutyl group, a 2,2,4,4-tetrafluorobutyl group, a 2,4,4,4-tetrafluorobutyl group, a 2,2,4,4,4-pentafluorobutyl group, a 3,3,3-trifluoro-2-trifluoromethylpropyl group, a 2,2,3,4,4,4-hexafluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a 4,4,4-trifluorobutyl group, a nonafluorobutyl group, a 4,4,4-trifluoro-3-trifluoromethylbutyl group, a 2,2-difluorobutyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a 5,5,5-trifluoropentyl group, a undecafluoropentyl group, a 5,5,5-trifluoro-4-trifluoromethylpentyl group, a 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group, a 6,6,6-trifluorohexyl group, a tridecafluorohexyl group, a 6,6,6-trifluoro-5-trifluoromethylhexyl group, a 2-fluoropentyl group, a 2,2-difluoropentyl group, a (2-fluoro-4-methyl)pentyl group, a (2,2-difluoro-4-methyl)pentyl group, a 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl group, a 7,7,7-trifluoroheptyl group, a pentadecafluoroheptyl group, a 7,7,7-trifluoro-6-trifluoromethylheptyl group, a (2-fluoro-4,4-dimethyl)pentyl group, a (2,2-difluoro-4,4-dimethyl)pentyl group, a 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl group, a 8,8,8-trifluorooctyl group, a heptadecafluorooctyl group, a 8,8,8-trifluoro-7-trifluoromethyloctyl group, a 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl group, a 9,9,9-trifluorononyl group, a nonadecafluorononyl group, a 9,9,9-trifluoro-8-trifluoromethylnonyl group, a 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecyl group, a 10,10,10-trifluorodecyl group, a henicosafluorodecyl group, a 10,10,10-trifluoro-9-trifluoromethyldecyl group, a 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-henicosafluoroundecyl group, a 11,11,11-trifluoroundecyl group and a tricosafluoroundecyl group.

The C3-C11 fluoroalkenyl group represents the C3-C11 alkenyl group having one or more fluorines.

Examples of the C3-C11 fluoroalkenyl group include a 2,3-difluoro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl group, a 1,1,2,3,3-pentafluoro-2-propenyl group, a 2,3-difluoro-2-butenyl group, a 4,4,4-trifluoro-2-butenyl group, a 4,4-difluoro-3-butenyl group, a 2-fluoro-2-butenyl group, a 3-fluoro-2-butenyl group, a 3,4,4-trifluoro-3-butenyl group, a 5,5,5-trifluoro-2-pentenyl group, a 5,5,5-trifluoro-3-pentenyl group, a 5,5,5-trifluoro-4-trifluoromethyl-2-pentenyl group, a 5,5-difluoro-4-pentenyl group, a 3,4-difluoro-3-pentenyl group, a 2-fluoro-2-pentenyl group, a 3-fluoro-2-pentenyl group, a 4,5,5-trifluoro-4-pentenyl group, a 2-fluoro-4-methyl-2-pentenyl group, a 2-fluoro-4,4-dimethyl-2-pentenyl group, a 6,6,6-trifluoro-2-hexenyl group, a 6,6,6-trifluoro-3-hexenyl group, a 6,6,6-trifluoro-5-trifluoromethyl-2-hexenyl group, a 6,6-difluoro-5-hexenyl group, a 7,7,7-trifluoro-2-heptenyl group, a 7,7,7-trifluoro-67-trifluoromethyl-2-heptenyl group, a 8,8,8-trifluoro-5-octenyl group, a 8,8,8-trifluoro-7-trifluoromethyl-3-octenyl group, a 9,9,9-trifluoro-2-nonenyl group, a 9,9,9-trifluoro-8-trifluoromethyl-2-nonenyl group, a 10,10,10-trifluoro-4-decenyl group, a 10,10,10-trifluoro-9-trifluoromethyl-8-decenyl group and a 11,11,11-trifluoro-2-undecenyl group.

The C3-C11 fluoroalkynyl group represents the C3-C11 alkynyl group having one or more fluorines.

Examples of the C3-C11 fluoroalkynyl group include a 1-fluoro-2-propynyl group, a 1,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-2-butynyl group, a 4-fluoro-2-butynyl group, a 4,4-difluoro-2-butynyl group, a 2-fluoro-3-butynyl group, a 5,5,5-trifluoro-3-pentynyl group, a 5,5,5-trifluoro-2-pentynyl group, a 4-fluoro-2-pentynyl group, a 5,5-difluoro-2-pentynyl group, a 2-fluoro-3-pentynyl group, a 2,5,5,5-tetrafluoro-3-pentynyl group, a 2,2,3,3-tetrafluoro-4-pentynyl group, a 3-fluoro-4-pentynyl group, a 5,5,6,6,6-pentafluoro-2-hexynyl group, a 6,6,6-trifluoro-5-trifluoromethyl-2-hexynyl group, a 7,7,7-trifluoro-3-heptynyl group, a 7,7,7-trifluoro-6-trifluoromethyl-2-heptynyl group, a 8,8,8-trifluoro-2-octynyl group, a 8,8,8-trifluoro-7-trifluoromethyl-4-octynyl group, a 9,9,9-trifluoro-2-nonyl group, a 9,9,9-trifluoro-8-trifluoromethyl-2-nonyl group, a 10,10,10-trifluoro-2-decynyl group, a 10,10,10-trifluoro-9-trifluoromethyl-6-decynyl group and a 11,11,11-trifluoro-5-undecynyl group.

Examples of C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group and an isopropyl group.

The C1-C6 alkyl group optionally having one or more halogens represents the C1-C6 alkyl group and the C1-C6 haloalkyl group.

Examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group and a hexyl group.

The C1-C6 haloalkyl group is the C1-C6 alkyl group having one or more halogen atoms, provided that when it has two or more halogen atoms, then the halogen atoms may be same or different.

Examples of the C1-C6 haloalkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, an undecafluoropentyl group, a tridecafluorohexyl group, a 2-chloropropyl group, a 2-bromopropyl group, a 2-iodopropyl group, a 6-chlorohexyl group, a 6-bromohexyl group and a 6-iodohexyl group.

Examples of the C3-C6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.

Examples of the amidine compound represent by the formula (1) include:

an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group; an amidine compound represented by the formula (1), wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R² is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R⁴ is a C1-C6 alkyl group optionally one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R⁴ is a methyl group and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R⁴ is a methyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R⁴ is a methyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R⁴ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group and R³ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens, R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is a methyl group and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is a methyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is a methyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R⁴ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a methyl group and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a methyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a methyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R³ is a methyl group, R⁴ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is C3-C6 a cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁴ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is C3-C6 a cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is C1-C6 a alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is C3-C6 a cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens, R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a methyl group and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a methyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a methyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R² is a methyl group, R³ is a methyl group, R⁴ is a methyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group optionally having one or more halogens; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C3-C6 cycloalkyl group and R⁵ is a C3-C6 cycloalkyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a methyl group; an amidine compound represented by the formula (1), wherein R¹ is a C1-C6 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkenyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; an amidine compound represented by the formula (1), wherein R¹ is a C3-C6 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group; and an amidine compound represented by the formula (1), wherein R¹ is a C7-C11 fluoroalkynyl group, R² is a methyl group, R³ is a methyl group, R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is an ethyl group.

(Production Method 1)

The present compound can be produced by reacting a compound represented formula (2) as follows (hereinafter referred to as Compound (2)) and a compound represented formula (3) as follows (hereinafter referred to as Compound (3)) in the presence of a base.

wherein R¹, R², R³, R⁴ and R⁵ are defined above, L represents chlorine, bromine, iodine, a methansulfonyloxy group, a trifluoromethanesulfonyloxy group or a p-toluenesulfonyloxy group.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran, ethyleneglycol dimethyl ether and tert-butyl methyl ether (hereinafter referred to as MTBE); aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbon such as chlorobenzene; nitriles such as acetonitrile; acid amides such as N,N-dimethylformamide (hereinafter referred to as DMF), 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone; sulfoxides such as dimethylsulfoxide; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; water and mixture thereof.

Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxydes such as sodium hydroxyde and potassium hydroxide and alkali metal hydride such as sodium hydride.

The amount of Compound (3) to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (2). The amount of base to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of −20 to 150° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

This reaction carried out in presence of sodium iodide and/or tetrabutylammonium iodide, if necessary. The amount of sodium iodide and/or tetrabutylammonium iodide to be used is usually 0.05 to 0.2 moles based on 1 mole of Compound (2).

After the completion of the reaction, the present compound can be isolated by carrying out post treatment operation such as extraction of the reaction mixture with an organic solvent drying of the organic layer and concentrate thereof. The present compound thus isolated can also be further purified by chromatography, re-crystallization and the like.

(Production Method 2)

The present compound can also be produced by the following method.

wherein R¹, R², R³, R⁴ and R⁵ are as defined above, and R⁶ represents a methyl group or an ethyl group.

(Process 1)

A compound represented formula (5) as below (hereinafter referred to as Compound (5)) can be produced by reacting a compound represented formula (4) as below (hereinafter referred to as Compound (4)); and trimethyl orthoformate or triethyl orthoformate in the presence of acid.

The reaction is usually carried out in the absence of a solvent.

Examples of the acid to be used in the reaction include sulfonic acids such as camphorsulfonic acid and p-toluenesulfonic acid; and inorganic acids such as hydrochloric acid and sulfuric acid.

The amount of trimethyl orthoformate or triethyl orthoformate to be used in the reaction is usually 1 mole to large excess amount based on 1 mole of Compound (4). The amount of the acid to be used in the reaction is usually 0.05 to 1 mole based on 1 mole of Compound (4).

The reaction temperature of the reaction is usually within a range of 80 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 2 hours.

After the completion of the reaction, Compound (5) can be isolated by concentrating the reaction mixture; or by carrying out post treatment operation such as extraction of the reaction mixture with an organic solvent, drying of the organic layer and concentrate thereof.

(Process 2)

The present compound can be produced by reacting Compound (5) and a compound represented formula (6) as below (hereinafter referred to as Compound (6)).

The reaction usually carried out in the presence of solvent.

Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran, ethyleneglycol dimethyl ether and MTBE; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbon such as chlorobenzene; nitriles such as acetonitrile; acid amides such as DMF, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone; sulfoxides such as dimethylsulfoxide; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone and mixture thereof.

The amount of compound (6) to be used in the reaction is usually 1 to 2 moles based on 1 mole of Compound (5).

The reaction temperature of the reaction is usually within a range of 80 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 3 hours.

After the completion of the reaction, the present compound can be isolated by concentrating the reaction mixture. The present compound thus isolated can also be further purified by chromatography.

(Production Method 3)

The present compound also can be produced by reacting Compound (4) and a compound represented formula (7) as follows (hereinafter referred to as Compound (7)).

wherein R¹, R², R³, R⁴ and R⁵ are as defined above, and R⁷ represents a methyl group or an ethyl group.

The reaction usually carried out in the presence of solvent.

Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran, ethyleneglycol dimethyl ether and MTBE; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbon such as chlorobenzene; nitriles such as acetonitrile; acid amides such as DMF, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone; sulfoxides such as dimethylsulfoxide; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone and mixture thereof.

The amount of compound (7) to be used in the reaction is usually 1 mole to large excess amount based on 1 mole of Compound (4).

The reaction temperature of the reaction is usually within a range of 80 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 2 hours.

After the completion of the reaction, the present compound can be isolated by concentrating the reaction mixture. The present compound thus isolated can also be further purified by chromatography.

In some cases, the present compound has cis-trans isomers, i.e., a cis isomer and a trans isomer, relative to the carbon atom bonded to the carbon atom of the double bond, and in the present invention, a compound containing one of such active isomers or both of them in any ratio can be used as the present compound.

Examples of the present compound are shown bellow with the number of the present compound.

A compound of the formula (1-A):

wherein R¹ represents a substituent shown in Tables 1-4:

TABLE 1 No. R¹ 1 2,2,3,4,4,4-hexafluorobutyl 2 2,2,3,3-tetrafluoropropyl 3 2,2,2-trifluoroethyl 4 2,2,3,3,3-pentafluoropropyl 5 2,2,3,3,4,4,4-heptafluorobutyl 6 2,2,3,3,4,4,5,5,5-nonafluoropentyl 7 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl 8 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl 9 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl 10 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl 11 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecyl 12 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11- henicosafluoroundecyl 13 monofluoromethyl 14 difluoromethyl 15 trifluoromethyl 16 pentafluoroethyl 17 3,3,3-trifluoropropyl 18 heptafluoropropyl 19 3,3,3-trifluoro-2-trifluoromethylpropyl 20 4,4,4-trifluorobutyl 21 nonafluorobutyl 22 4,4,4-trifluoro-3-trifluoromethylbutyl 23 2,2,4,4,4-pentafluorobutyl 24 5,5,5-trifluoropentyl 25 undecafluoropentyl 26 5,5,5-trifluoro-4-trifluoromethylpentyl

TABLE 2 No. R¹ 27 6,6,6-trifluorohexyl 28 tridecafluorohexyl 29 6,6,6-trifluoro-5-trifluoromethylhexyl 30 7,7,7-trifluoroheptyl 31 pentadecafluoroheptyl 32 7,7,7-trifluoro-6-trifluoromethylheptyl 33 8,8,8-trifluorooctyl 34 heptadecafluorooctyl 35 8,8,8-trifluoro-7-trifluoromethyloctyl 36 9,9,9-trifluorononyl 37 nonadecafluorononyl 38 9,9,9-trifluoro-8-trifluoromethylnonyl 39 10,10,10-trifluorodecyl 40 henicosafluorodecyl 41 10,10,10-trifluoro-9-trifluoromethyldecyl 42 11,11,11-trifluoroundecyl 43 tricosafluoroundecyl 44 2,3-difluoro-2-propenyl 45 4,4-difluoro-3-butenyl 46 5,5,5-trifluoro-4-trifluoromethyl-2-pentenyl 47 6,6,6-trifluoro-3-hexenyl 48 4,5-difluoro-4-heptenyl 49 8,8,8-trifluoro-4-octenyl 50 9,9,9-trifluoro-2-nonenyl 51 10,10,10-trifluoro-6-decenyl

TABLE 3 No. R¹ 52 11,11,11-trifluoro-7-undecenyl 53 1-fluoro-2-propynyl 54 4,4,4-trifluoro-2-butynyl 55 2,2,3,3-tetrafluoro-4-pentynyl 56 5,5,6,6,6-pentafluoro-2-hexynyl 57 7,7,7-trifluoro-3-heptynyl 58 8,8,8-trifluoro-5-octynyl 59 9,9,9-trifluoro-8-trifluoromethyl-2-nonynyl 60 10,10,10-trifluoro-4-decynyl 61 11,11,11-trifluoro-7-undecenyl 200 2-fluorobutyl 201 4-fluorobutyl 202 2,2-difluorobutyl 203 2,4-difluorobutyl 204 2,2,4-trifluorobutyl 205 2,4,4-trifluorobutyl 206 2,2,4,4-tetrafluorobutyl 207 2,4,4,4-tetrafluorobutyl 208 2,2,4,4,4-pentafluorobutyl 209 2-fluoropentyl 210 2,2-difluoropentyl

TABLE 4 No. R¹ 211 (2-fluoro-4-methyl)pentyl 212 (2,2-difluoro-4-methyl)pentyl 213 (2-fluoro-4,4-dimethyl)pentyl 214 (2,2-difluoro-4,4-dimethyl)pentyl 215 2-fluoro-2-pentenyl 216 2-fluoro-4-methyl-2-pentenyl 217 2-fluoro-4,4-dimethyl-2-pentenyl 218 2-fluoro-2-butenyl 219 4-fluoro-2-butenyl 220 2,4-difluoro-2-butenyl 221 4,4-difluoro-2-butenyl 222 2,4,4-trifluoro-2-butenyl 223 2,4,4,4-tetrafluoro-2-butenyl

A compound of the formula (1-B):

wherein R¹ represents a substituent shown in Tables 5-8:

TABLE 5 No. R¹ 62 2,2,3,4,4,4-hexafluorobutyl 63 2,2,3,3-tetrafluoropropyl 64 2,2,2-trifluoroethyl 65 2,2,3,3,3-pentafluoropropyl 66 2,2,3,3,4,4,4-heptafluorobutyl 67 2,2,3,3,4,4,5,5,5-nonafluoropentyl 68 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl 69 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl 70 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl 71 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl 72 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecyl 73 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11- henicosafluoroundecyl 74 monofluoromethyl 75 difluoromethyl 76 trifluoromethyl 77 pentafluoroethyl 78 3,3,3-trifluoropropyl 79 heptafluoropropyl 80 3,3,3-trifluoro-2-trifluoromethylpropyl 81 4,4,4-trifluorobutyl 82 nonafluorobutyl 83 4,4,4-trifluoro-3-trifluoromethylbutyl 84 2,2,4,4,4-pentafluorobutyl 85 5,5,5-trifluoropentyl 86 undecafluoropentyl 87 5,5,5-trifluoro-4-trifluoromethylpentyl

TABLE 6 No. R¹ 224 2-fluorobutyl 225 4-fluorobutyl 226 2,2-difluorobutyl 227 2,4-difluorobutyl 228 2,2,4-trifluorobutyl 229 2,4,4-trifluorobutyl 230 2,2,4,4-tetrafluorobutyl 231 2,4,4,4-tetrafluorobutyl 232 2,2,4,4,4-pentafluorobutyl 233 2-fluoropentyl 234 2,2-difluoropentyl 235 (2-fluoro-4-methyl)pentyl 236 (2,2-difluoro-4-methyl)pentyl 237 (2-fluoro-4,4-dimethyl)pentyl 238 (2,2-difluoro-4,4-dimethyl)pentyl 239 2-fluoro-2-pentenyl 240 2-fluoro-4-methyl-2-pentenyl 241 2-fluoro-4,4-dimethyl-2-pentenyl 242 2-fluoro-2-butenyl 243 4-fluoro-2-butenyl 244 2,4-difluoro-2-butenyl 245 4,4-difluoro-2-butenyl 246 2,4,4-trifluoro-2-butenyl 247 2,4,4,4-tetrafluoro-2-butenyl

TABLE 7 No. R¹ 88 6,6,6-trifluorohexyl 89 tridecafluorohexyl 90 6,6,6-trifluoro-5-trifluoromethylhexyl 91 7,7,7-trifluoroheptyl 92 pentadecafluoroheptyl 93 7,7,7-trifluoro-6-trifluoromethylheptyl 94 8,8,8-trifluorooctyl 95 heptafluorooctyl 96 8,8,8-trifluoro-7-trifluoromethyloctyl 97 9,9,9-trifluorononyl 98 nonadecafluorononyl 99 9,9,9-trifluoro-8-trifluoromethylnonyl 100 10,10,10-trifluorodecyl 101 henicosafluorodecyl 102 10,10,10-trifluoro-9-trifluoromethyldecyl 103 11,11,11-trifluoroundecyl 104 tricosafluoroundecyl 105 2,3-difluoro-2-propenyl 106 4,4-difluoro-3-butenyl 107 5,5,5-trifluoro-4-trifluoromethyl-2-pentenyl 108 6,6,6-trifluoro-3-hexenyl 109 4,5-difluoro-4-heptenyl 110 8,8,8-trifluoro-4-octenyl 111 9,9,9-trifluoro-2-nonenyl 112 10,10,10-trifluoro-6-decenyl

TABLE 8 No. R¹ 113 11,11,11-trifluoro-7-undecenyl 114 1-fluoro-2-propynyl 115 4,4,4-trifluoro-2-butynyl 116 2,2,3,3-tetrafluoro-4-pentynyl 117 5,5,6,6,6-pentafluoro-2-hexynyl 118 7,7,7-trifluoro-3-heptynyl 119 8,8,8-trifluoro-5-octynyl 120 9,9,9-trifluoro-8-trifluoromethyl-2-nonyl 121 10,10,10-trifluoro-4-decynyl 122 11,11,11-trifluoro-7-undecenyl

A compound of the formula (1-C):

wherein R², R³, R⁴ and R⁵ represent a combination shown in Tables 9-12:

TABLE 9 No. R² R³ R⁴ R⁵ 123 methyl methyl methyl propyl 124 methyl methyl methyl 1-methylethyl 125 methyl methyl methyl butyl 126 methyl methyl methyl 1-methylpropyl 127 methyl methyl methyl 2-methylpropyl 128 methyl methyl methyl 1,1-dimethylethyl 129 methyl methyl methyl pentyl 130 methyl methyl methyl 1-methylpentyl 131 methyl methyl methyl 2-methylpentyl 132 methyl methyl methyl 3-methylpentyl 133 methyl methyl methyl 4-methylpentyl 134 methyl methyl methyl hexyl 135 methyl methyl methyl cyclopropyl 136 methyl methyl methyl cyclobutyl 137 methyl methyl methyl cyclopentyl 138 methyl methyl methyl cyclohexyl 139 methyl methyl methyl monofluoromethyl 140 methyl methyl methyl difluoromethyl 141 methyl methyl methyl trifluoromethyl 142 methyl methyl methyl 2,2,2-trifluoroethyl 143 methyl methyl methyl 3,3,3-trifluoropropyl 144 methyl methyl methyl 4,4,4-trifluorobutyl 145 methyl methyl methyl 5,5,5-trifluoropentyl 146 methyl methyl methyl 6,6,6-trifluorohexyl

TABLE 10 No. R² R³ R⁴ R⁵ 147 methyl methyl monofluoromethyl trifluoromethyl 148 methyl methyl difluoromethyl trifluoromethyl 149 methyl methyl trifluoromethyl trifluoromethyl 150 methyl methyl 2,2,2-trifluoroethyl trifluoromethyl 151 methyl methyl 3,3,3-trifluoropropyl trifluoromethyl 152 methyl methyl 4,4,4-trifluorobutyl trifluoromethyl 153 methyl methyl 5,5,5-trifluoropentyl trifluoromethyl 154 methyl methyl 6,6,6-triflorohexyl trifluoromethyl 155 methyl methyl cyclopropyl trifluoromethyl 156 methyl methyl cyclobutyl trifluoromethyl 157 methyl methyl cyclopentyl trifluoromethyl 158 methyl methyl cyclohexyl trifluoromethyl 159 methyl methyl cyclopropyl cyclopropyl 160 methyl methyl cyclobutyl cyclopropyl 161 methyl methyl cyclopentyl cyclopropyl 162 methyl methyl cyclohexyl cyclopropyl 163 methyl methyl cyclobutyl cyclobutyl 164 methyl methyl cyclopentyl cyclobutyl 165 methyl methyl cyclohexyl cyclobutyl 166 methyl methyl cyclopentyl cyclopentyl 167 methyl methyl cyclohexyl cyclopentyl 168 methyl methyl cyclohexyl cyclohexyl 169 methyl ethyl methyl ethyl 170 methyl propyl methyl ethyl

TABLE 11 No. R² R³ R⁴ R⁵ 171 methyl 1-methylethyl methyl ethyl 172 ethyl methyl methyl ethyl 173 ethyl ethyl methyl ethyl 174 ethyl propyl methyl ethyl 175 ethyl 1-methylethyl methyl ethyl 176 propyl methyl methyl ethyl 177 propyl ethyl methyl ethyl 178 propyl propyl methyl ethyl 179 propyl 1-methylethyl methyl ethyl 180 1-methylethyl methyl methyl ethyl 181 1-methylethyl ethyl methyl ethyl 182 1-methylethyl propyl methyl ethyl 183 1-methylethyl 1-methylethyl methyl ethyl 184 methyl methyl methyl methyl 185 methyl ethyl methyl methyl 186 methyl propyl methyl methyl 187 methyl 1-methylethyl methyl methyl 188 ethyl methyl methyl methyl 189 ethyl ethyl methyl methyl 190 ethyl propyl methyl methyl 191 ethyl 1-methylethyl methyl methyl 192 propyl methyl methyl methyl 193 propyl ethyl methyl methyl 194 propyl propyl methyl methyl

TABLE 12 No. R² R³ R⁴ R⁵ 195 propyl 1-methylethyl methyl methyl 196 1-methylethyl methyl methyl methyl 197 1-methylethyl ethyl methyl methyl 198 1-methylethyl propyl methyl methyl 199 1-methylethyl 1-methylethyl methyl methyl 248 methyl methyl ethyl ethyl

A compound of the formula (1-D):

wherein R², R³, R⁴ and R⁵ represent a combination shown in Tables 13-17:

TABLE 13 No. R² R³ R⁴ R⁵ 249 methyl methyl methyl propyl 250 methyl methyl methyl 1-methylethyl 251 methyl methyl methyl butyl 252 methyl methyl methyl 1-methylpropyl 253 methyl methyl methyl 2-methylpropyl 254 methyl methyl methyl 1,1-dimethylethyl 255 methyl methyl methyl pentyl 256 methyl methyl methyl 1-methylpentyl 257 methyl methyl methyl 2-methylpentyl 258 methyl methyl methyl 3-methylpentyl 259 methyl methyl methyl 4-methylpentyl 260 methyl methyl methyl hexyl

TABLES 14 No. R² R³ R⁴ R⁵ 261 methyl methyl methyl cyclopropyl 262 methyl methyl methyl cyclobutyl 263 methyl methyl methyl cyclopentyl 264 methyl methyl methyl cyclohexyl 265 methyl methyl methyl monofluoromethyl 266 methyl methyl methyl difluoromethyl 267 methyl methyl methyl trifluoromethyl 268 methyl methyl methyl 2,2,2-trifluoroethyl 269 methyl methyl methyl 3,3,3-trifluoropropyl 270 methyl methyl methyl 4,4,4-trifluorobutyl 271 methyl methyl methyl 5,5,5-trifluoropentyl 272 methyl methyl methyl 6,6,6-triflluorohexyl 273 methyl methyl monofluoromethyl trifluoromethyl 274 methyl methyl difluoromethyl trifluoromethyl 275 methyl methyl trifluoromethyl trifluoromethyl 276 methyl methyl 2,2,2-trifluoroethyl trifluoromethyl 277 methyl methyl 3,3,3-trifluoropropyl trifluoromethyl 278 methyl methyl 4,4,4-trifluorobutyl trifluoromethyl 279 methyl methyl 5,5,5-trifluoropentyl trifluoromethyl 280 methyl methyl 6,6,6-trifluorohexyl trifluoromethyl

TABLE 15 No. R² R³ R⁴ R⁵ 281 methyl methyl cyclopropyl trifluoromethyl 282 methyl methyl cyclobutyl trifluoromethyl 283 methyl methyl cyclopentyl trifluoromethyl 284 methyl methyl cyclohexyl trifluoromethyl 285 methyl methyl cyclopropyl cyclopropyl 286 methyl methyl cyclobutyl cyclopropyl 287 methyl methyl cyclopentyl cyclopropyl 288 methyl methyl cyclohexyl cyclopropyl 289 methyl methyl cyclobutyl cyclobutyl 290 methyl methyl cyclopentyl cyclobutyl 291 methyl methyl cyclohexyl cyclobutyl 292 methyl methyl cyclopentyl cyclopentyl 293 methyl methyl cyclohexyl cyclopentyl 294 methyl methyl cyclohexyl cyclohexyl 295 methyl ethyl methyl ethyl 296 methyl propyl methyl ethyl 297 methyl 1-methylethyl methyl ethyl 298 ethyl methyl methyl ethyl 299 ethyl ethyl methyl ethyl 300 ethyl propyl methyl ethyl

TABLE 16 No. R² R³ R⁴ R⁵ 301 ethyl 1-methylethyl methyl ethyl 302 propyl methyl methyl ethyl 303 propyl ethyl methyl ethyl 304 propyl propyl methyl ethyl 305 propyl 1-methylethyl methyl ethyl 306 1-methylethyl methyl methyl ethyl 307 1-methylethyl ethyl methyl ethyl 308 1-methylethyl propyl methyl ethyl 309 1-methylethyl 1-methylethyl methyl ethyl 310 methyl methyl methyl methyl 311 methyl ethyl methyl methyl 312 methyl propyl methyl methyl 313 methyl 1-methylethyl methyl methyl

TABLE 17 No. R² R³ R⁴ R⁵ 314 ethyl methyl methyl methyl 315 ethyl ethyl methyl methyl 316 ethyl propyl methyl methyl 317 ethyl 1-methylethyl methyl methyl 318 propyl methyl methyl methyl 319 propyl ethyl methyl methyl 320 propyl propyl methyl methyl 321 propyl 1-methylethyl methyl methyl 322 1-methylethyl methyl methyl methyl 323 1-methylethyl ethyl methyl methyl 324 1-methylethyl propyl methyl methyl 325 1-methylethyl 1-methylethyl methyl methyl 326 methyl methyl ethyl ethyl

A compound of the formula (1-E):

wherein R², R³, R⁴ and R⁵ represent a combination shown in Tables 18-21:

TABLE 18 No. R² R³ R⁴ R⁵ 327 methyl methyl methyl propyl 328 methyl methyl methyl 1-methylethyl 329 methyl methyl methyl butyl 330 methyl methyl methyl 1-methylpropyl 331 methyl methyl methyl 2-methylpropyl 332 methyl methyl methyl 1,1-dimethylethyl 333 methyl methyl methyl pentyl 334 methyl methyl methyl 1-methylpentyl 335 methyl methyl methyl 2-methylpentyl 336 methyl methyl methyl 3-methylpentyl 337 methyl methyl methyl 4-methylpentyl 338 methyl methyl methyl hexyl 339 methyl methyl methyl cyclopropyl 340 methyl methyl methyl cyclobutyl 341 methyl methyl methyl cyclopentyl 342 methyl methyl methyl cyclohexyl 343 methyl methyl methyl monofluoromethyl 344 methyl methyl methyl difluoromethyl 345 methyl methyl methyl trifluoromethyl

TABLE 19 No. R² R³ R⁴ R⁵ 346 methyl methyl methyl 2,2,2-trifluoroethyl 347 methyl methyl methyl 3,3,3-trifluoropropyl 348 methyl methyl methyl 4,4,4-trifluorobutyl 349 methyl methyl methyl 5,5,5-trifluoropentyl 350 methyl methyl methyl 6,6,6-triflluorohexyl 351 methyl methyl monofluoromethyl trifluoromethyl 352 methyl methyl difluoromethyl trifluoromethyl 353 methyl methyl trifluoromethyl trifluoromethyl 354 methyl methyl 2,2,2-trifluoroethyl trifluoromethyl 355 methyl methyl 3,3,3-trifluoropropyl trifluoromethyl 356 methyl methyl 4,4,4-trifluorobutyl trifluoromethyl 357 methyl methyl 5,5,5-trifluoropentyl trifluoromethyl 358 methyl methyl 6,6,6-trifluorohexyl trifluoromethyl 359 methyl methyl cyclopropyl trifluoromethyl 360 methyl methyl cyclobutyl trifluoromethyl 361 methyl methyl cyclopentyl trifluoromethyl 362 methyl methyl cyclohexyl trifluoromethyl 363 methyl methyl cyclopropyl cyclopropyl 364 methyl methyl cyclobutyl cyclopropyl 365 methyl methyl cyclopentyl cyclopropyl 366 methyl methyl cyclohexyl cyclopropyl 367 methyl methyl cyclobutyl cyclobutyl 368 methyl methyl cyclopentyl cyclobutyl

TABLE 20 No. R² R³ R⁴ R⁵ 369 methyl methyl cyclohexyl cyclobutyl 370 methyl methyl cyclopentyl cyclopentyl 371 methyl methyl cyclohexyl cyclopentyl 372 methyl methyl cyclohexyl cyclohexyl 373 methyl ethyl methyl ethyl 374 methyl propyl methyl ethyl 375 methyl 1-methylethyl methyl ethyl 376 ethyl methyl methyl ethyl 377 ethyl ethyl methyl ethyl 378 ethyl propyl methyl ethyl 379 ethyl 1-methylethyl methyl ethyl 380 propyl methyl methyl ethyl 381 propyl ethyl methyl ethyl 382 propyl propyl methyl ethyl 383 propyl 1-methylethyl methyl ethyl 384 1-methylethyl methyl methyl ethyl 385 1-methylethyl ethyl methyl ethyl 386 1-methylethyl propyl methyl ethyl

TABLE 21 No. R² R³ R⁴ R⁵ 387 1-methylethyl 1-methylethyl methyl ethyl 388 methyl methyl methyl methyl 389 methyl ethyl methyl methyl 390 methyl propyl methyl methyl 391 methyl 1-methylethyl methyl methyl 392 ethyl methyl methyl methyl 393 ethyl ethyl methyl methyl 394 ethyl propyl methyl methyl 395 ethyl 1-methylethyl methyl methyl 396 propyl methyl methyl methyl 397 propyl ethyl methyl methyl 398 propyl propyl methyl methyl 399 propyl 1-methylethyl methyl methyl 400 1-methylethyl methyl methyl methyl 401 1-methylethyl ethyl methyl methyl 402 1-methylethyl propyl methyl methyl 403 1-methylethyl 1-methylethyl methyl methyl 404 methyl methyl ethyl ethyl

A compound of the formula (1-F):

wherein R², R³, R⁴ and R⁵ represent a combination shown in Tables 22-25:

TABLE 22 No. R² R³ R⁴ R⁵ 405 methyl methyl methyl propyl 406 methyl methyl methyl 1-methylethyl 407 methyl methyl methyl butyl

TABLES 23 No. R² R³ R⁴ R⁵ 408 methyl methyl methyl 1-methylpropyl 409 methyl methyl methyl 2-methylpropyl 410 methyl methyl methyl 1,1-dimethylethyl 411 methyl methyl methyl pentyl 412 methyl methyl methyl 1-methylpentyl 413 methyl methyl methyl 2-methylpentyl 414 methyl methyl methyl 3-methylpentyl 415 methyl methyl methyl 4-methylpentyl 416 methyl methyl methyl hexyl 417 methyl methyl methyl cyclopropyl 418 methyl methyl methyl cyclobutyl 419 methyl methyl methyl cyclopentyl 420 methyl methyl methyl cyclohexyl 421 methyl methyl methyl monofluoromethyl 422 methyl methyl methyl difluoromethyl 423 methyl methyl methyl trifluoromethyl 424 methyl methyl methyl 2,2,2-trifluoroethyl 425 methyl methyl methyl 3,3,3-trifluoropropyl 426 methyl methyl methyl 4,4,4-trifluorobutyl 427 methyl methyl methyl 5,5,5-trifluoropentyl 428 methyl methyl methyl 6,6,6-triflluorohexyl 429 methyl methyl monofluoromethyl trifluoromethyl 430 methyl methyl difluoromethyl trifluoromethyl 431 methyl methyl trifluoromethyl trifluoromethyl 432 methyl methyl 2,2,2-trifluoroethyl trifluoromethyl

TABLE 24 No. R² R³ R⁴ R⁵ 433 methyl methyl 3,3,3-trifluoropropyl trifluoromethyl 434 methyl methyl 4,4,4-trifluorobutyl trifluoromethyl 435 methyl methyl 5,5,5-trifluoropentyl trifluoromethyl 436 methyl methyl 6,6,6-trifluorohexyl trifluoromethyl 437 methyl methyl cyclopropyl trifluoromethyl 438 methyl methyl cyclobutyl trifluoromethyl 439 methyl methyl cyclopentyl trifluoromethyl 440 methyl methyl cyclohexyl trifluoromethyl 441 methyl methyl cyclopropyl cyclopropyl 442 methyl methyl cyclobutyl cyclopropyl 443 methyl methyl cyclopentyl cyclopropyl 444 methyl methyl cyclohexyl cyclopropyl 445 methyl methyl cyclobutyl cyclobutyl 446 methyl methyl cyclopentyl cyclobutyl 447 methyl methyl cyclohexyl cyclobutyl 448 methyl methyl cyclopentyl cyclopentyl 449 methyl methyl cyclohexyl cyclopentyl 450 methyl methyl cyclohexyl cyclohexyl 451 methyl ethyl methyl ethyl 452 methyl propyl methyl ethyl 453 methyl 1-methylethyl methyl ethyl 454 ethyl methyl methyl ethyl 455 ethyl ethyl methyl ethyl

TABLE 25 No. R² R³ R⁴ R⁵ 456 ethyl propyl methyl ethyl 457 ethyl 1-methylethyl methyl ethyl 458 propyl methyl methyl ethyl 459 propyl ethyl methyl ethyl 460 propyl propyl methyl ethyl 461 propyl 1-methylethyl methyl ethyl 462 1-methylethyl methyl methyl ethyl 463 1-methylethyl ethyl methyl ethyl 464 1-methylethyl propyl methyl ethyl 465 1-methylethyl 1-methylethyl methyl ethyl 466 methyl methyl methyl methyl 467 methyl ethyl methyl methyl 468 methyl propyl methyl methyl 469 methyl 1-methylethyl methyl methyl 470 ethyl methyl methyl methyl 471 ethyl ethyl methyl methyl 472 ethyl propyl methyl methyl 473 ethyl 1-methylethyl methyl methyl 474 propyl methyl methyl methyl 475 propyl ethyl methyl methyl 476 propyl propyl methyl methyl 477 propyl 1-methylethyl methyl methyl 478 1-methylethyl methyl methyl methyl 479 1-methylethyl ethyl methyl methyl 480 1-methylethyl propyl methyl methyl 481 1-methylethyl 1-methylethyl methyl methyl 482 methyl methyl ethyl ethyl

A compound of the formula (1-G):

wherein R², R³, R⁴ and R⁵ represent a combination shown in Tables 26-28:

TABLE 26 No. R² R³ R⁴ R⁵ 483 methyl methyl methyl propyl 484 methyl methyl methyl 1-methylethyl 485 methyl methyl methyl butyl 486 methyl methyl methyl 1-methylpropyl 487 methyl methyl methyl 2-methylpropyl 488 methyl methyl methyl 1,1-dimethylethyl 489 methyl methyl methyl pentyl 490 methyl methyl methyl 1-methylpentyl 491 methyl methyl methyl 2-methylpentyl 492 methyl methyl methyl 3-methylpentyl 493 methyl methyl methyl 4-methylpentyl 494 methyl methyl methyl hexyl 495 methyl methyl methyl cyclopropyl 496 methyl methyl methyl cyclobutyl 497 methyl methyl methyl cyclopentyl 498 methyl methyl methyl cyclohexyl 499 methyl methyl methyl monofluoromethyl 500 methyl methyl methyl difluoromethyl 501 methyl methyl methyl trifluoromethyl 502 methyl methyl methyl 2,2,2-trifluoroethyl

TABLE 27 No. R² R³ R⁴ R⁵ 503 methyl methyl methyl 3,3,3-trifluoropropyl 504 methyl methyl methyl 4,4,4-trifluorobutyl 505 methyl methyl methyl 5,5,5-trifluoropentyl 506 methyl methyl methyl 6,6,6-triflluorohexyl 507 methyl methyl monofluoromethyl trifluoromethyl 508 methyl methyl difluoromethyl trifluoromethyl 509 methyl methyl trifluoromethyl trifluoromethyl 510 methyl methyl 2,2,2-trifluoroethyl trifluoromethyl 511 methyl methyl 3,3,3-trifluoropropyl trifluoromethyl 512 methyl methyl 4,4,4-trifluorobutyl trifluoromethyl 513 methyl methyl 5,5,5-trifluoropentyl trifluoromethyl 514 methyl methyl 6,6,6-trifluorohexyl trifluoromethyl 515 methyl methyl cyclopropyl trifluoromethyl 516 methyl methyl cyclobutyl trifluoromethyl 517 methyl methyl cyclopentyl trifluoromethyl 518 methyl methyl cyclohexyl trifluoromethyl 519 methyl methyl cyclopropyl cyclopropyl 520 methyl methyl cyclobutyl cyclopropyl 521 methyl methyl cyclopentyl cyclopropyl 522 methyl methyl cyclohexyl cyclopropyl 523 methyl methyl cyclobutyl cyclobutyl 524 methyl methyl cyclopentyl cyclobutyl 525 methyl methyl cyclohexyl cyclobutyl

TABLE 28 No. R² R³ R⁴ R⁵ 526 methyl methyl cyclopentyl cyclopentyl 527 methyl methyl cyclohexyl cyclopentyl 528 methyl methyl cyclohexyl cyclohexyl 529 methyl ethyl methyl ethyl 530 methyl propyl methyl ethyl 531 methyl 1-methylethyl methyl ethyl 532 ethyl methyl methyl ethyl 533 ethyl ethyl methyl ethyl 534 ethyl propyl methyl ethyl 535 ethyl 1-methylethyl methyl ethyl 536 propyl methyl methyl ethyl 537 propyl ethyl methyl ethyl 538 propyl propyl methyl ethyl 539 propyl 1-methylethyl methyl ethyl 540 1-methylethyl methyl methyl ethyl 541 1-methylethyl ethyl methyl ethyl 542 1-methylethyl propyl methyl ethyl 543 1-methylethyl 1-methylethyl methyl ethyl 544 methyl methyl methyl methyl 545 methyl ethyl methyl methyl 546 methyl propyl methyl methyl 547 methyl 1-methylethyl methyl methyl 548 ethyl methyl methyl methyl 549 ethyl ethyl methyl methyl

TABLE 29 No. R² R³ R⁴ R⁵ 550 ethyl propyl methyl methyl 551 ethyl 1-methylethyl methyl methyl 552 propyl methyl methyl methyl 553 propyl ethyl methyl methyl 554 propyl propyl methyl methyl 555 propyl 1-methylethyl methyl methyl 556 1-methylethyl methyl methyl methyl 557 1-methylethyl ethyl methyl methyl 558 1-methylethyl propyl methyl methyl 559 1-methylethyl 1-methylethyl methyl methyl 560 methyl methyl ethyl ethyl

While the present controlling composition can be composed only of the present compound, it is usually used in a formulation form such as wettable powders, water dispersible granules, flowable concentrates, granules, dry flowable concentrates, emulsifiable concentrates, aqueous liquid formulations, oil formulations, smoking formulations, aerosols, microcapsules or the like, by mixing the present compound with a carrier (e.g., a solid, liquid or gaseous carrier), surfactants and auxiliary agents for formulation such as binders, dispersants and stabilizers. Such formulations usually contain the present compound in an amount of 0.1 to 99% by weight, preferably 0.2 to 90% by weight.

Examples of the solid carrier used for the formulation procedure include fine powders or particles of clays (e.g., kaolin, diatomaceous earth, synthetic hydrous silicon oxide fubasami clay, bentonite and acid clay), talc and other inorganic minerals (e.g., sericite, quartz powder, sulfur powder, activated carbon, calcium carbonate and hydrated silica); and examples of the liquid carrier include such as water, alcohols (e.g., methanol and ethanol), ketones (e.g., acetone and methyl ethyl ketone), aromatic hydrocarbons (e.g., benzene, toluene, xylene, ethylbenzene and methylnaphthalene), aliphatic or alicyclic hydrocarbons (e.g., n-hexane, cyclohexanone and kerosene), esters (e.g., ethyl acetate and butyl acetate), nitriles (e.g., acetonitrile and isobutyronitrile), ethers (e.g., dioxane and diisopropyl ether), acid amides (e.g., dimethylformamide and dimethylacetoamide) and halogenated hydrocarbons (e.g., dichloroethane, trichloroethylene and carbon tetrachloride).

Examples of the surfactant include such as alkyl sulfates, alkylsulfonates, alkylarylsulfonates, alkylaryl ethers and polyoxyethylenated products thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.

Examples of the other auxiliary agents for formulation include such as binders and dispersants. Specific example thereof include such as casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives and alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (e.g., polyvinyl alcohols, polyvinylpyrrolidones and polyacrylic acids), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, and fatty acids and esters thereof.

Although there is no particular limitation on a method for applying the present controlling agent in order to control plant diseases, the method is exemplified by treatment of plants such as foliar application, treatment of planting sites such as soil treatment, and treatment of seeds such as seed disinfection.

The present controlling agent can also be used in a mixture form with other fungicides, insecticides, acaricides or nematicides. It is also possible to use the present controlling agent simultaneously with such other chemicals without mixing with them.

Examples of the fungicides used with the present controlling agent include as follows.

(1) Azole Fungicides:

propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole cyproconazole, metconazole, triflumizole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, flutriafol, simeconazole, ipconazole, and the like;

(2) Amine Fungicides:

fenpropimorph, tridemorph, fenpropidin, spiroxamine, and the like;

(3) Benzimidazole Fungicides:

carbendazim, benomyl, thiabendazole, thiophanate-methyl, and the like;

(4) Dicarboxyimide Fungicides:

procymidone, iprodione, vinclozolin, and the like;

(5) Anilino Pyrimidine Fungicides:

cyprodinil, pyrimethanil, mepanipyrim, and the like;

(6) Phenylpyrrole Fungicides:

fenpiclonil, fludioxonil, and the like;

(7) Strobilurin Fungicides:

kresoxim-methyl, azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, pyribencarb, metominostrobin, orysastrobin, enestrobin, and the like;

(8) Phenyl Amide Fungicides:

metalaxyl, metalaxyl-M or mefenoxam, benalaxyl, benalaxyl-M or kiralaxyl, and the like;

(9) Carboxylic Acid Amide Fungicides:

dimethomorph, iprovalicarb, benthiavalicarb-isopropyl, mandipropamid, valiphenal;

(10) Carboxamide Fungicides:

carboxin, mepronil, flutolanil, thifluzamide, furametpyr, boscalid, penthiopyrad, fluopyram, bixafen, penflufen, sedaxane, fluxapyroxad and isopyrazam;

(11) Other Fungicides:

diethofencarb; thiuram; fluazinam; mancozeb; chlorothalonil; captan; dichlofluanid; folpet; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; cyazofamid; metrafenone; cyflufenamid; proquinazid; flusulfamide; fluopicolide; fosetyl; cymoxanil; pencycuron; tolclofos-methyl; carpropamid; diclocymet; fenoxanil; tricyclazole; pyroquilon; probenazole; isotianil; tiadinil; tebufloquin; diclomezine; kasugamycin; ferimzone; fthalide; validamycin; hydroxyisoxazole; iminoctadine acetate; isoprothiolane; oxolinic acid; oxytetracycline; streptomycin; basic copper chloride; copper (II) hydroxide; basic copper sulfate; organic copper; sulfur; ametoctradin; fenpyrazamine, and the like; an α-alkoxyphenylacetic acid compound represented by the formula (12):

wherein X³ represents a methyl group, a difluoromethyl group or an ethyl group; X⁴ represents a methoxy group or a methylamino group; and X⁵ represents a phenyl group, a 2-methylphenyl group or a 2,5-dimethylphenyl group.

Examples of the insecticides used with the present controlling agent include as follows.

(1) Organic Phosphorus Compounds:

acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos:CYAP, diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion:ECP, dichlorvos:DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion:MPP, fenitrothion:MEP, fosthiazate, formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion:DMTP, monocrotophos, naled:BRP, oxydeprofos:ESP, parathion, phosalone, phosmet:PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate:PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon:DEP, vamidothion, phorate, cadusafos, and the like;

(2) Carbamate Compounds:

alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb:MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur:PHC, XMC, thiodicarb, xylylcarb, aldicarb, and the like;

(3) Synthetic Pyrethroid Compounds:

acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, furamethrin, tau-fluvalinate, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, and the like;

(4) Nereistoxin Compounds:

cartap, bensultap, thiocyclam, monosultap, bisultap, and the like;

(5) Neonicotinoid Compounds:

imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin, and the like;

(6) Benzoyl Urea Compounds:

chlorfluazuron, bistrifluoron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, and the like;

(7) Phenylpyrazole-Based Compounds:

acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, and the like;

(8) Bt Toxin Insecticides:

Living spores, produced crystalline toxins and the mixtures thereof derived form Baccilus thuringiensis;

(9) Hydrazine Compounds:

chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and the like;

(10) Organic Chlorine Compounds:

aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, and the like;

(11) Natural Insecticides:

machine oil and nicotine-sulfate;

(12) Other Insecticides:

avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, D-D(1,3-Dichloropropene), emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, Methyl bromide, nidinotefuran, Potassium oleate, protrifenbute, spiromesifen, Sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, chlorantraniliprole and cyantrannileprole.

Examples of the acaricides (acaricidal active ingredients) used with the present controlling agent include such as acequinocyl, amitraz, benzoximate, bifenazate, bromopropylate, chinomethionate, chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite:BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet and cyenopyrafen.

Examples of the acaricides (acaricidal active ingredients) used with the present controlling agent include such as acequinocyl, amitraz, benzoximate, bifenazate, bromopropylate, chinomethionate, chlorobenzilate, CPCBS(chlorfenson), clofentezine, cyflumetofen, dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite:BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet and cyenopyrafen.

Examples of the nematocides (nematocidal active ingredients) used with the present controlling agent include such as DCIP, fosthiazate, levamisol, methylsothiocyanate, morantel tartarate and imicyafos.

Although the applying dosage of the present controlling agent is varied depending on weather conditions, formulation forms, when, how and where the present controlling agent is applied, target diseases, target crops and the like, it is usually 1 to 500 g, preferably 2 to 200g, per 1000 m² in terms of the present compound in the present controlling agent. When the present controlling agent takes a form of emulsifiers, wettable powders, suspensions or the like, it is usually applied after diluted with water. In this case, the concentration of the present compound after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight. When the present controlling agent takes a form of powders, granules or the like, it is applied as it is without dilution. In an application to seeds, the applying dosage is usually in a range from 0.001 to 100 g, preferably 0.01 to 50 g, per kilogram of seed in terms of the present compound in the present controlling agent.

The present controlling agent can be used as a controlling composition for plant diseases in crop lands such as upland field, paddy field, lawn and turf, orchard and the like. The present controlling agent is able to control plant diseases in the crop lands or the like where the following “crops” and the like are cultivated.

Field crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rape, sunflower, sugarcane, tobacco, etc.

Vegetables: solanaceae (e.g. eggplant, tomato, green pepper, chili pepper and potato), Cucurbitaceae (e.g. cucumber, pumpkin, zucchini, watermelon and melon), Cruciferae (e.g. Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli and cauliflower), Compositae (e.g. edible burdock, garland chrysanthemum, globe artichoke and lettuce), Liliacede (e.g., Welsh onion, onion, garlic and asparagus), Umbelliferae (e.g. carrot, parsley, celery and parsnip), Chenopodiaceae (e.g. spinach and chard), Lamiaceae (e.g. perilla, mint and basil), strawberry, sweet potato, Chinese yam, taro, jatropha, etc.

Flowers and ornament plants.

Ornamental foliage plants.

Fruit trees: pomaceous fruits (e.g. apple, pear, Japanese pear, Chinese quince and quince), stone fruits (e.g. peach, plum, nectarine, Japanese apricot, yellow peach, apricot and prune), citrus fruits (e.g. satsuma mandarin, orange, lemon, lime and grapefruit), nut trees (e.g. chestnut, walnut, hazel, almond, pistachio, cashew nut and macadamia nut), berries (blueberry, cranberry, blackberry and raspberry), grape, Japanese persimmon, olive, loquat, banana, coffee, date palm, coconut, etc.

Trees other than fruit trees: tea, mulberry, flowering trees and shrubs, street trees (e.g. Japanese ash, birch, flowering dogwood, blue gum, ginkgo, lilac, maple, oak, poplar, Chinese redbud, Formosa sweet gum, plane tree, zelkova, Japanese arborvitae, fir, Japanese hemlock, needle juniper, pine, Japanese spruce and Japanese yew), etc.

The above-mentioned “crops” also include those imparted with resistance to herbicides, such as HPPD inhibitors (e.g., isoxaflutole), ALS inhibitors (e.g., imazethapyr and thifensulfuron-methyl), EPSP synthetase inhibitors, glutamine synthetase inhibitors, bromoxynil and dicamba, by way of a classic breeding method or genetic recombination technology.

Examples of the “crops” imparted with resistance by the classic breeding method include Clearfield® canola resistant to imidazolinone-based herbicides (e.g., imazethapyr), STS soybean resistant to sulfonylurea-based ALS inhibition type herbicides such as thifensulfuron-methyl, or the like. Further, examples of the crops imparted with resistance by the genetic recombination technology include corn cultivars resistant to glyphosate and gluphosinate, which have been already on the market under the trade name of RoundupReady®, RoundupReady 2® and LibertyLink®.

The above-mentioned “crops” also include plants in which the genetic recombination technology has enabled to synthesize, for example, a selective toxin known as genus Bacillus.

Examples of toxins produced in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; insecticidal proteins such as δ-endotoxins (e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C), VIP1, VIP2, VIP3 and VIP3A, which are derived from Bacillus thuringiensis; toxins derived from nematodes; toxins produced by animals, such as scorpion toxin, spider toxin, bee toxin and insect-specific neurotoxins; filamentous fungi toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitor, patatin, cystatin and papain inhibitors; ribosome-inactivating proteins (RIP) such as ricin, corn-RIP, abrin, rufin, sapolin and priodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitors; HMG-COA reductase; ion channel inhibitors such as a sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone acceptors; stilbene synthetase; bibenzyl synthetase; chitinase; and glucanase.

The toxins produced in such genetically modified crops also include hybrid toxins, partially deficient toxins and modified toxins of insecticidal proteins, such as 5-endotoxin proteins (e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C), VIP1, VIP2, VIP3 and VIP3A. The hybrid toxins are produced by a novel combination of the different domains of such a protein by adopting recombination technology. The known partially deficient toxin is Cry1Ab, in which a part of amino acid sequence is deficient. In the modified toxins, one or a plurality of amino acids of a natural toxin are replaced.

Examples of such toxins and genetically modified plants capable of synthesizing such toxins are described in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878, WO 03/052073, etc.

The toxins contained in such genetically modified plants impart resistance to insect pests of Coleoptera, insect pests of Diptera and insect pests of Lepidoptera to the plants.

Further, it has already been known that there are genetically modified plants containing one or a plurality of insecticidal pest-resistant genes and capable of producing one or a plurality of toxins. Some of them are commercially available. Examples of such genetically modified plants include such as YieldGard® (a corn cultivar capable of producing a Cry1Ab toxin), YieldGard Rootworm® (a corn cultivar capable of producing a Cry3Bb1 toxin), YieldGard Plus® (a corn cultivar capable of producing Cry1Ab and Cry3Bb1 toxins), Herculex I® (a corn cultivar capable of producing phosphinotrysin N-acetyltransferase (PAT) for imparting resistance to a Cry1Fa2 toxin and Glufosinate), NuCOTN33B (a cotton cultivar capable of producing a Cry1Ac toxin), Bollgard I® (a cotton cultivar capable of producing a Cry1Ac toxin), Bollgard II® (a cotton cultivar capable of producing Cry1Ab and Cry2Ab toxins), VIPCOT® (a cotton cultivar capable of producing a VIP toxin), NewLeaf® (a potato cultivar capable of producing a Cry3A toxin), NatureGard® Agrisure® GT Advantage (GA21 Glyphosate resistant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

The above-mentioned “crops” also include those imparted with an ability of producing an anti-pathogenic substance having selective action, by way of genetic recombination technology.

As examples of the anti-pathogenic substance, PR proteins and the like are known (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants capable of producing them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191, etc.

Examples of such anti-pathogenic substances produced by the genetically modified plants include ion channel inhibitors, such as sodium channel inhibitors and calcium channel inhibitors (for example, KP1, KP4 and KP6 toxins produced by viruses are known); stilbene synthases; bibenzyl synthases; chitinase; glucanase; PR proteins; and anti-pathogenic substances produced by microorganisms, such as peptide antibiotics, antibiotics having a heterocyclic ring and protein factors involved in plant disease resistance (which are called as plant-disease-resistant genes and are described in WO 03/000906), etc.

Examples of plant diseases controllable by the present invention include such as fungal diseases. More specifically, the following plant diseases are listed, but the diseases are not limited thereto.

The present controlling method is usually practiced in the method, wherein the present controlling agent is applied in the above-mentioned manner.

Blast (Magnaporthe grisea), Brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani) and “Bakanae” disease (Gibberella fujikuroi) of rice;

powdery mildew (Erysiphe graminis), scab (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), Snow mold (Micronectriella nivale), Typhula snow blight (Typhula sp.), loose smut (Ustilago tritici), bunt (Tilletia caries), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Stagonospora nodorum) and tan spot (Pyrenophora tritici-repentis) of wheat;

powdery mildew (Erysiphe graminis), scab (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), loose smut (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), spot blotch (Cochliobolus sativus), leaf stripe (Pyrenophora graminea) and seedling damping-off by Rhizoctonia genus (Rhizoctonia solani) of barley;

melanose (Diaporthe citri), scab (Elsinoe fawcetti) and Penicillium rot (Penicillium digitatum, P. italicum) of citrus;

blossom blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype),

scab (Venturia inaequalis) and anthracnose (Glomerella cingulata) of apple;

scab (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pathotype) and rust (Gymnosporangium haraeanum) of pear;

brown rot (Monilinia fructicola), scab (Cladosporium carpophilum) and Phomopsis rot (Phomopsis sp.) of peach;

anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii) and downy mildew (Plasmopara viticola) of grape;

anthracnose (Gloeosporium kaki) and leaf spot (Cercospora kaki, Mycosphaerella nawae) of Japanese persimmon;

anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Mycosphaerella melonis), stem rot (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), Phytophthora rot (Phytophthora sp.) and seedling blight (Pythium sp.) of melons and cucumber;

early blight (Alternaria solani), leaf mold (Cladosporium fulvum) and leaf blight (Phytophthora infestans) of tomato;

brown spot (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum) of eggplant;

Alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae) and downy mildew (peronospora parasitica) of vegetables of Crusiferae;

Welsh onion rust (Puccinia allii);

purple stain (Cercospora kikuchii), Sphaceloma scab (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var. sojae) and rust (Phakopsora pachyrhizi) of soybean;

kidney bean anthracnose (Colletotrichum lindemthianum);

leaf spot (Cercospora personata), leaf spot (Cercospora arachidicola) and southern blight (Sclerotium rolfsii) of peanut;

pea powdery mildew (Erysiphe pisi);

early blight (Alternaria solani), late blight (Phytophthora infestans) and Verticillium wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens) of potato;

strawberry powdery mildew (Sphaerotheca humuli);

net blister blight (Exobasidium reticulatum);

white scab (Elsinoe leucospila), zonate leaf spot (Pestalotiopsis sp.) and anthracnose (Colletotrichum theae-sinensis) of tea plant;

brown spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina) and Phytophthora rot (Phytophthora nicotianae) of tobacco;

leaf spot (Cercospora beticola), foliage blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris) and black root rot (Aphanomyces cochlioides) of beet;

black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa) of rose;

leaf blight (Septoria chrysanthemi-indici) and white rust (Puccinia horiana) of chrysanthemum;

Botrytis diseases (Botrytis cinerea, B. byssoidea, B. squamosa), gray mold neck rot (Botrytis alli) and Small sclerotial neck rot (Botrytis squamosa) of onion;

gray mold (Botrytis cinerea) and stem rot (Sclerotinia sclerotiorum) of various crops;

Alternaria leaf spot (Alternaria brassicicola) of Japanese radish;

dollar spot (Sclerotinia homeocarpa), brown patch and large patch (Rhizoctonia solani) of turf grass; and

Sigatoka diseases (Mycosphaerella fijiensis, Mycosphaerella musicola, Pseudocercospora musae) of banana.

EXAMPLES

The present invention will be explained in more detail by way of Preparation Examples, Formulation Examples and Test Examples, which should not be construed as limiting the present invention. All the “parts” are by weight. Preparation Example 1 of the present compound

To 40 ml of chloroform, 5.6 g of 2,2,3,4,4,4-hexafluorobutanol was added at room temperature, and to the mixture, 3.0 ml of pyridine and 6.2 ml of trifluoromethanesulfonic anhydride were added at 0° C., and the mixture was stirred at room temperature for 1 hour and 30 minutes. To the reaction mixture, 1N of hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave 4.15 g of crude of 2,2,3,4,4,4-hexafluorobutyl trifluoromethanesulfonate.

To 10 ml of DMF, 0.50 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, then, to the mixture, 0.11 g of 60% sodium hydride (oil dispersion) was added, and the mixture was stirred at room temperature for 20 minutes. Then, to the mixture, 0.92 g of crude of 2,2,3,4,4,4-hexafluorobutyl trifluoromethanesulfonate obtained above was added at room temperature, and the mixture was stirred at room temperature for 2 hours and 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extract with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure.

The resultant residue was subjected to silica gel column chromatography to obtain 0.5 g of the formula:

(hereinafter referred to as “the present compound 1”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.18-4.38 (2H, m), 5.11-5.28 (1H, m), 6.56 (1H, s), 6.63 (1H, s), 7.38 (1H, s).

Preparation Example 2 of the Present Compound

To 3 ml of DMF, 0.20 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, then, to the mixture, 0.26 g of 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate and 0.11 g of 60% sodium hydride (oil dispersion) were added successively at room temperature, and the mixture was stirred overnight. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.20 g of the formula:

(hereinafter referred to as “the present compound 2”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.1 Hz), 2.16 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.28 (2H, t, J=11.8 Hz), 6.08 (1H, tt, J=53.0, 5.2 Hz), 6.56 (1H, s), 6.62 (1H, s), 7.38 (1H, s).

Preparation Example 3 of the Present Compound

To 20 ml of diethyl ether, 0.70 g of 2,2,2-trifluoroethanol was added at room temperature and to the mixture, 1.4 ml of trifluoromethanesulfonic anhydride and 1.0 ml of triethylamine were added at −50° C., and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 0.46 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate.

To the 4 ml of DMF, 0.22 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.047 g of 60% sodium hydride (oil dispersion) was added at room temperature, and the mixture was stirred at room temperature for 15 minutes. Then, to the mixture, 0.30 g of crude of 2,2,2-trifluoroethyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 2 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.15 g of formula:

(hereinafter referred to as “the present compound 3”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.19 (3H, s), 2.22 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.29 (2H, q, J=8.3 Hz), 6.56 (1H, s), 6.62 (1H, s), 7.39 (1H, s).

Preparation Example 4 of the Present Compound

To 40 ml of diethyl ether, 1.5 g of 2,2,3,3,3-pentafluoropropanol was added at room temperature. To the mixture, 2.0 ml of trifluoromethanesulfonic anhydride and 1.5 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate.

To 10 ml of DMF, 0.53 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.15 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 20 minutes. Then to the mixture, whole amount of crude of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.094 g of formula:

(hereinafter referred to as “the present compound 4”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.34 (2H, br s), 4.34-4.37 (2H, m), 6.56 (1H, s), 6.60 (1H, s), 7.38 (1H, s).

Preparation Example 5 of the Present Compound

To 30 ml of diethyl ether, 1.6 g of 2,2,3,3,4,4,4-heptafluorobutanol was added at room temperature, and to the mixture, 1.6 ml of trifluoromethanesulfonic anhydride and 1.1 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of 2,2,3,3,4,4,4-heptafluorobutyl trifluoromethanesulfonate.

To 10 ml of DMF, 0.48 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.14 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 20 minutes. To the mixture, whole amount of crude of 2,2,3,3,4,4,4-heptafluorobutyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 20 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.059 g of formula:

(hereinafter referred to as “the present compound 5”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.39 (2H, t, J=12.9 Hz), 6.56 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 6 of the Present Compound

To 25 ml of diethyl ether, 1.5 g of 2,2,3,3,4,4,5,5,5-nonafluoropentanol was added at room temperature, and to the mixture, 1.2 ml of trifluoromethanesulfonic anhydride and 0.89 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of 2,2,3,3,4,4,5,5,5-nonafluoropentyl trifluoromethanesulfonate.

To 3 ml of DMF, 0.20 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.043 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 15 minutes. To the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,5-nonafluoropentyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 1 hour. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.045 g of formula:

(hereinafter referred to as “the present compound 6”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.40 (2H, t, J=12.9 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 7 of the Present Compound

To 20 ml of diethyl ether, 1.9 g of 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanol was added at room temperature, and to the mixture, 1.2 ml of trifluoromethanesulfonic anhydride and 0.91 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl trifluoromethanesulfonate.

To 3 ml of DMF, 0.20 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.078 g of 60% sodium hydride (oil dispersion) was added at room temperature, then, the mixture was stirred at room temperature for 30 minutes. To the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 2 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.083 g of formula:

(hereinafter referred to as “the present compound 7”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.18 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.40 (2H, t, J=12.9 Hz), 6.56 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 8 of the Present Compound

To 20 ml of diethyl ether, 2.1 g of 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanol was added at room temperature. To the mixture, 1.2 ml of trifluoromethanesulfonic anhydride and 0.89 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl trifluoromethanesulfonate.

To the 3 ml of DMF, 0.20 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.078 g of 60% sodium hydride (oil dispersion) was added, then the mixture was stirred at room temperature for 30 minutes. Then to the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 2 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.065 g of formula:

(hereinafter referred to as “the present compound 8”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.40 (2H, t, J=12.9 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 9 of the Present Compound

To 30 ml of diethyl ether, 2.5 g of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanol was added at room temperature, and to the mixture, 1.3 ml of trifluoromethanesulfonic anhydride and 0.92 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadefluorooctyl trifluoromethanesulfonate.

To the 10 ml of DMF, 0.50 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.16 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 20 minutes. Then to the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadefluorooctyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 2 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.082 g of formula:

(hereinafter referred to as “the present compound 9”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.1 Hz), 2.18 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.40 (2H, t, J=12.8 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 10 of the Present Compound

To 30 ml of diethyl ether, 3.1 g of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononanol was added at room temperature, and to the mixture, 1.4 ml of trifluoromethanesulfonic anhydride and 1.0 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 10 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptafluorononyl trifluoromethanesulfonate.

To the 3 ml of DMF, 0.20 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.16 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 15 minutes. To the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptafluorononyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 15 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.094 g of formula:

(hereinafter referred to as “the present compound 10”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.18 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.40 (2H, t, J=12.8 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 11 of the Present Compound

To 20 ml of diethyl ether, 2.5 g of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecanol was added at room temperature, and to the mixture, 1.0 ml of trifluoromethanesulfonic anhydride and 0.74 ml of triethylamine were successively added at −50° C., and the mixture was stirred at 0° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added, and extracted with diethyl ether. The organic layer was washed successively with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue gave crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecyl trifluoromethanesulfonate.

To the 10 ml of DMF, 0.51 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.20 g of 60% sodium hydride (oil dispersion) was added at room temperature, then the mixture was stirred at room temperature for 15 minutes. Then to the mixture, whole amount of crude of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecyl trifluoromethanesulfonate obtained above was added at room temperature, and stirred at room temperature for 2 hours and 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.12 g of formula:

(hereinafter referred to as “the present compound 11”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.18 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.36 (2H, br s), 4.40 (2H, t, J=13.0 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.39 (1H, s).

Preparation Example 12 of the Present Compound

To the 6 ml of DMF, 0.26 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine was added at room temperature, and to the mixture, 0.055 g of 60% sodium hydride (oil dispersion) and 0.95 g of 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-henicosafluoroundecyl trifluoromethanesulfonate were successively added at 0° C., then the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.059 g of formula:

(hereinafter referred to as “the present compound 12”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.2 Hz), 2.18 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.35 (2H, br s), 4.41 (2H, t, J=12.8 Hz), 6.57 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 13 of the Present Compound

To 7 ml of DMF, 0.43 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine and 0.031 g of sodium iodide were added at room temperature, and to the mixture, 0.055 g of 60% sodium hydride (oil dispersion) was added at room temperature, then stirred at room temperature for 30 minutes. To the mixture, 0.59 g of 1-bromo-4,4,4-trifluorobutane was added at room temperature, then the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.11 g of formula:

(hereinafter referred to as “the present compound 13”).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J=7.0 Hz), 2.02-2.05 (2H, m), 2.15 (3H, s), 2.23 (3H, s), 2.30-2.33 (2H, m), 2.97 (3H, s), 3.35 (2H, br s), 3.97 (2H, t, J=5.9 Hz), 6.55 (1H, s), 6.61 (1H, s), 7.39 (1H, s).

Preparation Example 14 of the Present Compound

To 7 ml of DMF, 0.44 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine and 0.032 g of sodium iodide were added at room temperature, and to the mixture, 0.093 g of 60% sodium hydride (oil dispersion) was added at room temperature, then stirred at room temperature for 30 minutes. To the mixture, 0.59 g of 1-bromo-6,6,6-trifluorohexane was added at room temperature, then the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.16 g of formula:

(hereinafter referred to as “the present compound 14”).

¹H-NMR (CDCl₃) δ: 1.19 (3H, t, J=7.2 Hz), 1.60-1.64 (4H, m), 1.76-1.83 (2H, m), 2.08-2.11 (2H, m), 2.15 (3H, s), 2.23 (3H, s), 2.97 (3H, s), 3.34 (2H, br s), 3.92 (2H, t, J=6.1 Hz), 6.55 (1H, s), 6.62 (1H, s), 7.39 (1H, s).

Preparation Example 15 of the Present Compound

To 0.26 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 4 ml of trimethyl orthoformate and 0.018 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, and extracted with MTBE. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of Methyl N-{4-(2,2-difluoro-4,4-dimethylpentyloxy)-2,5-dimethyl}phenylformimidate.

To 4 ml of 1,4-dioxane, whole amount of crude of Methyl N-{4-(2,2-difluoro-4,4-dimethylpentyloxy)-2,5-dimethyl}phenylformimidate obtained above was added at room temperature. To the mixture, 0.12 ml of ethylmethylamine was added at room temperature, and stirred at 80° for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then, the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.22 g of formula:

(hereinafter referred to as “the present compound 15”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.19 (3H, t, J=7.2 Hz), 2.01 (2H, t, J=20.0 Hz), 2.20 (3H, s), 2.22 (3H, s), 2.97 (3H, s), 3.34 (2H, br s), 4.00 (2H, t, J=12.0 Hz), 6.55 (1H, s), 6.59 (1H, s), 7.38 (1H, s).

Preparation Example 16 of the Present Compound

To 0.25 g of 2,2-difluoro-(4-amino-2,5-dimethylphenoxy)butane, 4 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 1 hour and 40 minutes. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, and extracted with MTBE. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of Methyl N-{4-(2,2-difluorobutoxy)-2,5-dimethyl}phenylformimidate.

To 4 ml of 1,4-dioxane, whole amount of crude of Methyl N-{4-(2,2-difluorobutoxy)-2,5-dimethyl}phenylformimidate obtained above was added. To the mixture, 0.14 ml of ethylmethylamine was added at room temperature, and stirred at 80° C. for 40 minutes. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.25 g of formula:

(hereinafter referred to as “the present compound 16”).

¹H-NMR (CDCl₃) δ: 1.08 (3H, t, J=7.6 Hz), 1.19 (3H, t, J=7.1 Hz), 2.04-2.15 (2H, m), 2.17 (3H, s), 2.23 (3H, s), 2.98 (3H, s), 3.34 (2H, br s), 4.07 (2H, t, J=11.7 Hz), 6.56 (1H, s), 6.61 (1H, s), 7.38 (1H, s).

Preparation Example 17 of the Present Compound

To 0.28 g of 2,2-difluoro-4-methyl-(4-amino-2,5-dimethylphenoxy)pentane, 4 ml of trimethyl orthoformate and 0.020 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 1 hour and 40 minutes. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, and extracted with MTBE. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue gave a crude of Methyl N-{4-(2,2-difluoro-4-methylpentyloxy)-2,5-dimethylphenyl}formimidate.

To 4 ml of 1,4-dioxane, whole amount of crude of Methyl N-{4-(2,2-difluoro-4-methylpentyloxy)-2,5-dimethylphenyl}formimidate obtained above was added. To the mixture, 0.14 ml of ethylmethylamine was added at room temperature, and stirred at 80° C. for 40 minutes. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.28 g of formula:

(hereinafter referred to as “the present compound 17”).

¹H-NMR (CDCl₃) δ: 1.01 (6H, d, J=6.3 Hz), 1.19 (3H, t, J=7.0 Hz), 1.95-1.99 (3H, m), 2.18 (3H, s), 2.23 (3H, s), 2.97 (3H, s), 3.34 (2H, br s), 4.05 (2H, t, J=11.8 Hz), 6.56 (1H, s), 6.61 (1H, s), 7.39 (1H, s).

Preparation Example 18 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane and 0.23 ml of diethylamine were added at room temperature, then the mixture was stirred at 80° C. for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.20 g of formula:

(hereinafter referred to as “the present compound 18”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.20 (6H, t, J=7.1 Hz), 2.01 (2H, t, J=20.2 Hz), 2.19 (3H, s), 2.22 (3H, s), 3.37 (4H, br s), 4.00 (2H, t, J=12.0 Hz), 6.55 (1H, s), 6.59 (1H, s), 7.36 (1H, s).

Preparation Example 19 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of N,N-dimethylformamide dimethyl acetal was added at room temperature, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.22 g of formula:

(hereinafter referred to as “the present compound 19”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 2.01 (2H, t, J=20.0 Hz), 2.19 (3H, s), 2.23 (3H, s), 2.99 (6H, s), 4.00 (2H, t, J=12.0 Hz), 6.56 (1H, s), 6.59 (1H, s), 7.37 (1H, s).

Preparation Example 20 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane and 0.23 ml of N-methylpropylamine were added at room temperature, then the mixture was stirred at 80° C. for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.19 g of formula:

(hereinafter referred to as “the present compound 20”).

¹H-NMR (CDCl₃) δ: 0.92 (3H, t, J=7.4 Hz), 1.09 (9H, s), 1.62 (2H, m), 2.01 (2H, t, J=20.2 Hz), 2.19 (3H, s), 2.22 (3H, s), 2.97 (3H, s), 3.22 (2H, br s), 4.00 (2H, t, J=12.0 Hz), 6.55 (1H, s), 6.59 (1H, s), 7.39 (1H, s).

Preparation Example 21 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane and 0.23 ml of N-methylisopropylamine were added at room temperature, then the mixture was stirred at 80° C. for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.17 g of formula:

(hereinafter referred to as “the present compound 21”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.22 (6H, d, J=6.8 Hz), 2.01 (2H, t, J=20.0 Hz), 2.19 (3H, s), 2.22 (3H, s), 2.88 (3H, s), 3.36 (1H, br s), 4.00 (2H, t, J=12.0 Hz), 6.56 (1H, s), 6.59 (1H, s), 7.45 (1H, s).

Preparation Example 22 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 2.5 hours. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane, 0.24 g of N-methylcyclopropylamine hydrochloride and 1 ml of triethylamine were added at room temperature, then, the mixture was stirred at 80° C. for 3 hours. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, 5% hydrochloric acid was added, and extracted with ethyl acetate. The organic layer was successively washed with water, an aqueous saturated sodium hydrogen carbonate solution and saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.16 g of formula:

(hereinafter referred to as “the present compound 22”).

¹H-NMR (CDCl₃) δ: 0.69-0.75 (4H, m), 1.09 (9H, s), 2.01 (2H, t, J=20.0 Hz), 2.19 (3H, s), 2.22 (3H, s), 2.66 (1H, m), 3.01 (3H, s), 4.01 (2H, t, J=12.0 Hz), 6.55 (1H, s), 6.59 (1H, s), 7.57 (1H, s).

Preparation Example 23 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane and 0.22 g of N-methylcyclopentylamine were added at room temperature, then the mixture was stirred at 80° C. for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then, the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.26 g of formula:

(hereinafter referred to as “the present compound 23”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.59-1.74 (6H, m), 1.86-1.90 (2H, m), 2.01 (2H, t, J=20.2 Hz), 2.19 (3H, s), 2.23 (3H, s), 2.90-2.93 (4H, m), 4.00 (2H, t, J=12.0 Hz), 6.56 (1H, s), 6.59 (1H, s), 7.48 (1H, s).

Preparation Example 24 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane and 0.25 g of N-methylcyclohexylamine were added at room temperature, then the mixture was stirred at 80° C. for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then, the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.26 g of formula:

(hereinafter referred to as “the present compound 24”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.23-1.40 (4H, m), 1.44-1.57 (2H, m), 1.83 (4H, m), 2.01 (2H, t, J=20.2 Hz), 2.19 (3H, s), 2.22 (3H, s), 2.92 (3H, s), 3.12 (1H, br s), 4.00 (2H, t, J=12.0 Hz), 6.56 (1H, s), 6.59 (1H, s), 7.47 (1H, s).

Preparation Example 25 of the Present Compound

To 0.30 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane, 5 ml of trimethyl orthoformate and 0.021 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature and concentrated under reduced pressure. To the resultant residue, 5 ml of 1,4-dioxane, 1 ml of triethylamine and 0.27 g of N-methylcyclobutylamine were added at room temperature, then the mixture was stirred at 80° C. for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then, the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.23 g of formula:

(hereinafter referred to as “the present compound 25”).

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 1.62-1.77 (2H, m), 2.01 (2H, t, J=20.0 Hz), 2.19-2.22 (10H, m), 2.94-2.96 (4H, m), 4.01 (2H, t, J=12.0 Hz), 6.55 (1H, s), 6.59 (1H, s), 7.44 (1H, s).

Preparation Example 26 of the Present Compound

To 0.51 g of (Z)-2-fluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)penta-2-ene, 8 ml of trimethyl orthoformate and 0.038 g of para-toluenesulfonic acid monohydrate were added at room temperature, and the mixture was refluxed for hour. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate was added, then extract with MTBE. The organic layer was washed with saturated brine, and concentrated under reduced pressure. The resultant residue gave a crude of Methyl N—[(Z)-{2-fluoro-4,4-dimethylpent-2-enyloxy}-2,5-dimethyl]phenylformimidate

To 8 ml of 1,4-dioxane, whole amount of the crude of Methyl N—[(Z)-{2-fluoro-4,4-dimethylpent-2-enyloxy}-2,5-dimethyl]phenylformimidate obtained above was added at room temperature. Then, to the mixture, 0.26 ml of ethylmethylamine was added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, then, the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.31 g of formula:

(hereinafter referred to as “the present compound 26”).

¹H-NMR (CDCl₃) δ: 1.01 (9H, s), 1.20 (3H, t, J=7.0 Hz), 2.05 (2H, d, J=25.1 Hz), 2.22 (6H, s), 2.98 (3H, s), 3.35 (2H, br s), 5.79 (1H, d, J=21.0 Hz), 6.55 (1H, s), 6.73 (1H, s), 7.39 (1H, s).

Preparation Example 27 of the Present Compound

To 0.38 g of 4,4,4-trifluoro-(4-amino-2,5-dimethylphenoxy)but-2-yne, 5 ml of N,N-dimethylformamide dimethylacetal was added at room temperature. The mixture was stirred at 90° C. for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature, then the reaction mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.22 g of formula:

(hereinafter referred to as “the present compound 27”).

¹H-NMR (CDCl₃) δ: 2.18 (3H, s), 2.24 (3H, s), 2.99 (6H, s), 4.73 (2H, q, J=3.1 Hz), 6.56 (1H, s), 6.69 (1H, s), 7.38 (1H, s).

Next, reference production examples will be shown for illustrating production of a production intermediate of the present compound.

Reference Production Example 1

To 10 g of 4-hydroxy-2,5-dimethylaniline, 60 ml of trimethyl orthoformate and 1.4 g of para-toluenesulfonic acid monohydrate were added, and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature, then, to the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added. The mixture was concentrated under reduced pressure. The resultant residue was washed with an aqueous saturated sodium hydrogen carbonate solution and mixed solvent of hexane and MTBE successively, and gave 13 g of Methyl N-(4-hydroxy-2,5-dimethylphenyl)formimidate.

Methyl N-(4-hydroxy-2,5-dimethylphenyl)formimidate

¹H-NMR (CDCl₃) δ: 2.17 (3H, s), 2.19 (3H, s), 3.87 (3H, s), 6.55 (1H, s), 6.61 (1H, s), 7.64 (1H, s).

To 13 g of Methyl N-(4-hydroxy-2,5-dimethylphenyl)formimidate, 200 ml of 1,4-dioxane was added at room temperature. To the mixture, 12 ml of ethylmethylamine was added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, and concentrated under reduced pressure. The resulting solid was collected by filtration and washed with MTBE to obtain 8.1 g of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methyformamidine.

N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylormamidine

¹H-NMR (CDCl₃) δ: 1.19 (3H, t, J=7.2 Hz), 2.18 (3H, s), 2.19 (3H, s), 2.97 (3H, s), 3.34 (2H, br s), 6.51 (1H, s), 6.58 (1H, s), 7.38 (1H, s).

Reference Production Example 2

To 1.0 litre of acetonitrile, 2,5-dimethyl-4-hydroxybenzene and 44 g of potassium carbonate were added at room temperature. To the mixture, 56 g of bromomethyl (2,2-dimethylpropyl)ketone was added at room temperature, then the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature, then filtered through Celite®, and the filtrate was concentrated under reduced pressure. To the resultant residue, water was added, and extracted with MTBE. The organic layer was successively washed with 1% aqueous sodium hydroxide solution and saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 72 g of 4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one.

4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one

¹H-NMR (CDCl₃) δ: 1.07 (9H, s), 2.32 (3H, s), 2.48 (2H, s), 2.59 (3H, s), 4.59 (2H, s), 6.47 (1H, s), 7.95 (1H, s).

To 22 g of 4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one, 52 g of bis(2-methoxyethyl)aminosulfur trifluoride was added, and the mixture was stirred at 70° C. for 5 hours and 30 minutes. The reaction mixture was allowed to stand and cooled to about room temperature, diluted with MTBE. The obtained dilution was poured into water, and extracted with MTBE. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine successively, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain g of 2,2-difluoro-4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentane.

To 13 g of 2,2-difluoro-4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentane, 450 ml of chloroform and 200 ml of methanol were added at room temperature. An ozone gas was blown into the mixture with stirring at the range of −40° C. to −35° C. for 1 hour. A nitrogen gas was blown into the mixture with stirring at the range of −40° C. to −35° C. for 30 minutes. To the mixture, 8.8 g of sodium borohydride was added at the range of −40° C. to −35° C., and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture, conc. HCl was added until pH value of the mixture had reached to more than 10, and concentrated under reduced pressure. To the resultant residue, water was added, and extracted with MTBE. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine successively, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 13 g of 2,2-difluoro-4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentane.

2,2-difluoro-4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentane

¹H-NMR (CDCl₃) δ: 1.10 (9H, s), 2.01 (2H, t, J=20.0 Hz), 2.27 (3H, s), 2.62 (3H, s), 4.13 (2H, t, J=11.6 Hz), 6.63 (1H, s), 7.94 (1H, s).

13 g of 2,2-difluoro-4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentane, 0.9 g of 10% paradium carbon was added, then to the mixture, 150 ml of ethanol was added. The mixture was stirred under 0.40 Mpa of hydrogen gas atmosphere for 3 hours. The reaction mixture was filtered through Celite®, and the filtrate was concentrated under reduced pressure to obtain 11 g of 2,2-difluoro-(4-amino-2,5-dimethylphenoxy)pentane.

2,2-difluoro-(4-amino-2,5-dimethylphenoxy)pentane

¹H-NMR (CDCl₃) δ: 1.09 (9H, s), 2.00 (2H, t, J=20.1 Hz), 2.14 (3H, s), 2.16 (3H, s), 3.97 (2H, t, J=12.0 Hz), 6.52 (1H, s), 6.54 (1H, s).

Reference Production Example 3

To 10 ml of DMF, 1.0 g of 2,5-dimethyl-4-hydroxybromobenzene and 0.69 g of potassium carbonate were added. To the mixture, 0.72 g of bromomethyl ethyl ketone was added at room temperature, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture, water was added and extracted with MTBE. The organic layer was washed with an aqueous 1% sodium hydroxide solution and a saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was washed with mixed-solvent of hexane and MTBE to obtain 0.78 g of (4-bromo-2,5-dimethylphenoxy)butan-2-one.

(4-bromo-2,5-dimethylphenoxy)butan-2-one

¹H-NMR (CDCl₃) δ: 1.12 (3H, t, J=7.2 Hz), 2.24 (3H, s), 2.33 (3H, s), 2.66 (2H, q, J=14.1 Hz), 4.51 (2H, s), 6.53 (1H, s), 7.31 (1H, s).

To 10 ml of chloroform, 0.52 g of (4-bromo-2,5-dimethylphenoxy)butan-2-one was added. To the mixture, 0.40 ml of diethylaminosulfur trifluoride was added at 0° C., and stirred at room temperature for 13 hours and 30 minutes. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.38 g of 2,2-difluoro-(4-bromo-2,5-dimethylphenoxy)butane.

2,2-difluoro-(4-bromo-2,5-dimethylphenoxy)butane

¹H-NMR (CDCl₃) δ: 1.08 (3H, t, J=7.6 Hz), 2.05-2.12 (2H, m), 2.17 (3H, s), 2.35 (3H, s), 4.08 (2H, t, J=11.5 Hz), 6.66 (1H, s), 7.29 (1H, s).

To 0.56 g of 2,2-difluoro-(4-bromo-2,5-dimethylphenoxy)butane, 0.088 g of tris(dibenzylideneacetone)dipalladium, 0.63 g of triphenylsilylamine and 0.080 g of 2-(dicyclohexylphosphino)biphenyl were added at room temperature. To the mixture, 2.5 ml of 1N solution in toluene of lithium hexamethyldisilazide was added, and the mixture was stirred at 100° C. for 9 hours. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, 10 ml of 1N hydrochloric acid was added, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added until pH value of the mixture had reached to less than 10, then, extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.34 g of 2,2-difluoro-(4-amino-2,5-dimethylphenoxy)butane.

2,2-difluoro-(4-amino-2,5-dimethylphenoxy)butane

¹H-NMR (CDCl₃) δ: 1.07 (3H, t, J=7.6 Hz), 2.03-2.12 (2H, m), 2.13 (3H, s), 2.15 (3H, s), 3.34 (2H, br s), 4.03 (2H, t, J=11.7 Hz), 6.51 (1H, s), 6.56 (1H, s).

Reference Production Example 4

To 30 ml of DMF, 2.0 g of 2,5-dimethyl-4-hydroxybromobenzene and 1.4 g of potassium carbonate were added. To the mixture, 1.7 g of bromomethyl 2-methylpropyl ketone was added at room temperature, then the mixture was stirred at room temperature for 2 hours. To the reaction mixture, water was added, then extracted with MTBE. The organic layer was washed with an aqueous 1% sodium hydroxide solution and saturated brine successively, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was washed with mixed-solvent of hexane and MTBE to obtain 1.7 g of 4-methyl-2,5-dimethyl-4-bromophenoxy)pentan-2-one.

4-methyl-2,5-dimethyl-4-bromophenoxy)pentan-2-one

¹H-NMR (CDCl₃) δ: 0.96 (6H, d, J=6.8 Hz), 2.22-2.25 (4H, m), 2.32 (3H, s), 2.48 (2H, d, J=6.8 Hz), 4.48 (2H, s), 6.51 (1H, s), 7.31 (1H, s).

To 15 ml of chloroform, 1.2 g of 4-methyl-2,5-dimethyl-4-bromophenoxy)pentan-2-one was added at room temperature. To the mixture, 0.45 ml of diethylaminosulfur trifluoride was added at 0° C., the mixture was stirred at room temperature for 15 hours and 30 minutes. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, then extracted with chloroform. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.62 g of 2,2-difluoro-4-methyl-(2,5-dimethyl-4-bromophenoxy)pentane.

2,2-difluoro-4-methyl-(2,5-dimethyl-4-bromophenoxy)pentane

¹H-NMR (CDCl₃) δ: 1.02 (6H, d, J=5.9 Hz), 1.94-1.98 (3H, m), 2.18 (3H, s), 2.35 (3H, s), 4.06 (2H, t, J=11.6 Hz), 6.65 (1H, s), 7.29 (1H, s).

To 0.56 g of 2,2-difluoro-4-methyl-(2,5-dimethyl-4-bromophenoxy)pentane, 0.080 g of tris(dibenzilideneacetone)dipalladium, 0.58 g of triphenylsilylamine and 0.074 g of 2-(dicyclohexylphosphino)biphenyl were added at room temperature. To the mixture, 2.3 ml of 1N toluene solution of lithium hexamethyldisilazide was added, and stirred at 100° C. for 8 hours and 30 minutes. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, 10 ml of 1N hydrochloric acid was added, then, the mixture was stirred at room temperature for 1 hour and 30 minutes. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added until pH value of the mixture had reached to less than 10, then, extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.33 g of 2,2-difluoro-4-methyl-(2,5-dimethyl-4-aminophenoxy)pentane.

2,2-difluoro-4-methyl-(2,5-dimethyl-4-aminophenoxy)pentane

¹H-NMR (CDCl₃) δ: 1.01 (6H, d, J=6.1 Hz), 1.90-2.01 (3H, m), 2.13 (3H, s), 2.16 (3H, s), 3.34 (2H, br s), 4.01 (2H, t, J=11.8 Hz), 6.51 (1H, s), 6.55 (1H, s).

Reference Production Example 5

To 20 ml of 1,4-dioxane, 1.2 g of 2,2-difluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentane was added. To the mixture, 3.1 g of potassium tert-butoxide was added, then the mixture was refluxed for 7 hours. The reaction mixture was allowed to stand and cooled to about room temperature. To the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.51 g of (Z)-2-fluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentan-2-ene.

(Z)-2-fluoro-4,4-dimethyl-(4-amino-2,5-dimethylphenoxy)pentan-2-ene

¹H-NMR (CDCl₃) δ: 1.00 (9H, s), 2.12 (3H, s), 2.20 (3H, s), 3.38 (2H, br s), 4.55 (2H, s), 5.72 (1H, d, J=21.3 Hz), 6.50 (1H, s), 6.68 (1H, s).

Reference Production Example 6

To 200 ml of toluene, 10 g of 2,5-dimethyl-4-hydroxynitrobenzene, 7.5 g of 4,4,4-trifluorobutan-2-ol and 16 g of triphenylphosphine were added at room temperature. To the mixture, 27 ml of 2.2 M toluene solution of diethyl azodicarboxylate was added at 0° C., then, the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, then the resultant residue was subjected to silica gel column chromatography and recrystallization from mixed solvent of hexane and chloroform to obtain 1.5 g of 4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one. Then, the mother liquid obtained by the recrystallization was concentrated. The resulting residue was subjected to silica gel column chromatography and recrystallization from mixed solvent of hexane and chloroform to obtain 0.8 g of 4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one.

4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one

¹H-NMR (CDCl₃) δ: 2.26 (3H, s), 2.64 (3H, s), 4.90 (2H, q, J=3.0 Hz), 6.71 (1H, s), 7.94 (1H, s).

To 4 ml of water, 2.0 g of iron powder, 1.9 g of 4,4-dimethyl-(2,5-dimethyl-4-nitrophenoxy)pentan-2-one and 28 ml of acetic acid were added at room temperature, and stirred at 80° C. for 1 hour and 30 minutes. The reaction mixture was allowed to stand and cooled to about room temperature, then filtered through Celite®. The filterate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography and high performance liquid chromatography successively to obtain 0.38 g of 4,4,4-trifluoro-(4-amino-2,5-dimethylphenoxy)butan-2-yne.

4,4,4-trifluoro-(4-amino-2,5-dimethylphenoxy)butan-2-yne

¹H-NMR (CDCl₃) δ: 2.14 (3H, s), 2.15 (3H, s), 3.37 (2H, br s), 4.67 (2H, q, J=3.1 Hz), 6.50 (1H, s), 6.64 (1H, s).

Formulation Example 1

Fifty parts of any one of the present compounds 1-27, 3 parts of calcium ligninsulfonate, 2 parts of magnesium laurylsulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a formulation.

Formulation Example 2

Twenty parts of any one of the present compounds 1-27 and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is pulverized by wet pulverizing method. Then, 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added thereto, and further added 10 parts of propylene glycol, followed by stirring and mixing to obtain a formulation.

Formulation Example 3

Two parts of any one of the present compounds 1-27, 88 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a formulation.

Formulation Example 4

Five parts of any one of the present compounds 1-27, 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are thoroughly mixed to obtain a formulation.

Formulation Example 5

Two parts of any one of the present compound 1-27, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, then water is added thereto, followed by thoroughly kneading and granulation drying to obtain a formulation.

Formulation Example 6

Ten parts of any one of the present compound 1-27, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed, and the mixture is pulverized by wet pulverizing method to obtain a formulation.

Hereinafter, usefulness of the present compounds for controlling plant diseases is shown by test examples.

Here, the controlling effect was evaluated by comparing the area of lesions on test plants treated with the present compound with that on untreated plants through visual observation of the area of lesion on the test plant at testing.

Test Example 1

A Plastic pot was stuffed with soil, then, rice plant (plant variety; Nihonbare) was sowed on this, and allowed to grow in a greenhouse for 20 days. Each of the present compounds 1, 15 and 22 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown rice. After the foliage application, the plant was air-dried and then grown in contact with a rice seedling (plant variety; Nihonbare) infected with blast fungus (Magnaporthe grisea), for 6 days at 24° C. and a high humidity in the daytime and at 20° C. and a high humidity in the nighttime. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 1, 15 and 22 was 30% or less of the area of lesions on an untreated plant.

Test Example 2

A plastic pot was stuffed with soil, then, wheat (variety; Shirogane) was sown on this, and allowed to grow in a greenhouse for 9 days. Then the plant was inoculated with spores of leaf rust (Puccinia recondita) by sprinkling. After inoculation the plant was allowed to stand under dark and highly humid condition at 23° C. for one day, then, the plant was air-dried. Each of the present compounds 1 and 2 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of grown wheat. After completion of the foliar application, the plant was air-dried, and allowed to stand for 7 days under illumination, then, the lesion area was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 1 and 2 was 30% or less of the area of lesions on an untreated plant.

Test Example 3

A Plastic pot was stuffed with soil, then, wheat (variety; Shirogane) was sowed on this, and allowed to grow in a greenhouse for 9 days. Each of the present compounds 1, 2, 3, 4, 5, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 and 26 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown rice. After the foliage application, the plant was air-dried and allowed to stand at 18° C. for 5 days under illumination. Then the plant was inoculated with spores of leaf rust (Puccinia recondita) by sprinkling. After inoculation the plant was first allowed to stand under dark for one day, further, allowed to stand at 18° C. under illumination for 8 days, then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 1, 2, 3, 4, 5, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 and 26 was 30% or less of the area of lesions on an untreated plant.

Test Example 4

A Plastic pot was stuffed with soil, then, cucumber (plant variety; Sagamihanjiro) was sowed on this, and allowed to grow in a greenhouse for 12 days. Each of the present compounds 1, 2, 3, 4, 5, 8, 9, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22 and 26 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown cucumber. After completion of the foliar application, the plant was air-dried, and inoculated with spores of powdery mildew (Sphaerotheca fuliginea) by sprinkling. After inoculation the plant was placed in a greenhouse for 11 days at 24° C. in the daytime and at 20° C. in the nighttime. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 1, 2, 3, 4, 5, 8, 9, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22 and 26 was 30% or less of the area of lesions on an untreated plant.

Test Example 5

A Plastic pot was stuffed with soil, then, wheat (variety: Apogee) was sowed on this, and allowed to grow in a greenhouse for 10 days. Each of the present compounds 1, 8, 15, 16, 18, 19, 20, 21, 22, 24 and 25 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown wheat. After completion of the foliar application, the plant was air-dried, and two days after, inoculated with an aqueous suspension of Septoria tritici spores by spraying. After inoculation, the plant was first allowed to stand at 18° C. and a high humidity for 3 days, further, allowed to stand for 14 to 18 days under illumination, then, the lesion area was investigated. As a result, the lesion area on the plant treated with each of the present compounds 1, 8, 15, 16, 18, 19, 20, 21, 22, 24 and 25 was 30% or less of the area of lesions on an untreated plant.

Test Example 6

A Plastic pot was stuffed with soil, then, barley (variety; Nishinohoshi) was sown on this, and allowed to grow in a greenhouse for 7 days. Each of the present compounds 1, 2, 8, 13, 14, 15, 16, 17, 20, 21, 22, 23 and 25 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown barley. After completion of the foliar application, the plant was air-dried, and two days after, inoculated with an aqueous suspension of Pyrenophora teres spores by spraying. After inoculation, the plant was first allowed to be placed in a greenhouse for 3 days at 23 C and a high humidity in the daytime and at 20° C. and a high humidity in the nighttime, further, allowed to stand for 7 days in greenhouse, then the lesion area was investigated. As a result, the lesion area on the plant treated with each of the present compounds 1, 2, 8, 13, 14, 15, 16, 17, 20, 21, 22, 23 and 25 was 30% or less of the area of lesions on an untreated plant.

Test Example 7

A Plastic pot was stuffed with soil, then, cucumber (plant variety; Sagamihanjiro) was sowed on this, and allowed to grow in a greenhouse for 12 days. Each of the present compounds 6 and 7 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 50 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown cucumber. After completion of the foliar application, the plant was air-dried, and inoculated with spores of powdery mildew (Sphaerotheca fuliginea) by sprinkling. After inoculation the plant was placed in a greenhouse for 11 days at 24° C. in the daytime and at 20° C. in the nighttime. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 6 and 7 was 30% or less of the area of lesions on an untreated plant.

Test Example 8

A Plastic pot was stuffed with soil, then, barley (variety; Nishinohoshi) was sown on this, and allowed to grow in a greenhouse for 7 days. The present compound 7 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 50 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown barley. After completion of the foliar application, the plant was air-dried, and two days after, inoculated with an aqueous suspension of Pyrenophora teres spores by spraying. After inoculation, the plant was first allowed to be placed in a greenhouse for 3 days at 23° C. and a high humidity in the daytime and at 20° C. and a high humidity in the nighttime, further, allowed to stand for 7 days in greenhouse, then, the lesion area was investigated. As a result, the lesion area on the plant treated with the present compound 7 was 30% or less of the area of lesions on an untreated plant.

Test Example 9

A plastic pot was stuffed with soil, then, wheat (variety; Shirogane) was sown on this, and allowed to grow in a greenhouse for 9 days. Then the plant was inoculated with spores of leaf rust (Puccinia recondita) by sprinkling. After inoculation the plant was allowed to stand under dark and highly humid condition at 23° C. for one day, then, the plant was air-dried. Each of the present compounds 6 and 7 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 50 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of grown wheat. After completion of the foliar application, the plant was air-dried, and allowed to stand for 7 days under illumination, then, the lesion area was investigated. As a result, it was found that the area of lesions on the plant treated with each of the present compounds 6 and 7 was 30% or less of the area of lesions on an untreated plant.

Test Example 10

A Plastic pot was stuffed with soil, then, soybean (variety; Kurosengoku) was sown on this, and allowed to grow in a greenhouse for 13 days. Then the plant was inoculated with an aqueous suspension of Phakopsora pachyrhizi spores by spraying. After inoculation the plant was allowed to stand under dark and highly humid condition at 23° C. for one day, then, the plant was air-dried. Each of the present compounds 15, 26 and 27 was formulated according to Formulation Example 2, and the formulation was diluted with water so that the concentration of active ingredients was 200 ppm. Then, the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown soybean. After completion of the foliar application, the plant was air-dried, and allowed to stand for 14 days under illumination, then, the lesion area was investigated. As a result, the lesion area on the plant treated with each of the present compounds 15, 26 and 27 was 30% or less of the area of lesions on an untreated plant.

INDUSTRIAL APPLICABILITY

As described hereinabove, the present compound has excellent plant disease controlling effect and hence is useful as an active ingredient of plant disease controlling agents. 

1. An amidine compound represented by the formula (1):

wherein R¹ represent a C1-C11 fluoroalkyl group, a C3-C11 fluoroalkenyl group or a C3-C11 fluoroalkynyl group; R² represent a C1-C3 alkyl group; R³ represent a C1-C3 alkyl group; R⁴ represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens and R⁵ represent a C3-C6 cycloalkyl group or a C1-C6 alkyl group optionally having one or more halogens.
 2. The amidine compound according to claim 1, wherein R⁴ is a C1-C6 alkyl group optionally having one or more halogens and R⁵ is a C1-C6 alkyl group having one or more halogens.
 3. The amidine compound according to claim 1, wherein R⁴ is a C1-C6 alkyl group and R⁵ is a C1-C6 alkyl group.
 4. A plant disease controlling agent, which comprises the amidine compound according to claim 1 as an active ingredient.
 5. A method for controlling plant diseases, which comprises the step of applying an effective amount of the amidine compound according to claim 1 to plants or soils.
 6. Use of the amidine compound according to claim 1 for controlling plant diseases. 